Lower alkyl 2-[[N-(3-cyano-pyridin-2-yl)aminocarbonyl]aminosulphonyl]benzoate derivatives having herbicidal activity

ABSTRACT

Certain N-[(pyridyl or pyrimidyl)aminocarbonyl]arylsulfonamides, such as the compound methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]aminosulfonyl]benzoate, possess herbicidal activity.

RELATED APPLICATION

This application is a continuation-in-part of my copending application U.S. Ser. No. 591,314, filed Mar. 23, 1984 now abandoned which is a continuation-in-part of my copending application U.S. Ser. No. 493,079, filed May 9, 1983, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel N-[(pyridyl or pyrimidyl)aminocarbonyl]arylsulfonamides, to herbicidal compositions containing them and to methods of using them to control the growth of undesired vegetation.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situtations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

A number of different types of N-[(heterocyclic)aminocarbonyl]arylsulfonamides are known as herbicides. Two of the first patents to issue on such compounds are U.S. Pat. Nos. 4,169,719 and 4,127,405, issued on Oct. 2, 1979 and Nov. 28, 1978, respectively. These patents disclose compounds of the general formula ##STR1## where R₁ can be optionally substituted benzene, thiophene, pyrrole, furan or unsubstituted naphthalene, and Y is N or CH.

Subsequent patents which have issued have disclosed related compounds with different N-heterocycles. For example, U.S. Pat. No. 4,293,330, issued on Oct. 6, 1981, discloses pyridyl sulfonylureas, and U.S. Pat. No. 4,221,585, issued on Sept. 9, 1980, disclose 4-pyrimidyl sulfonylureas. Nowhere in the art has there been any indication that N-(pyridyl or pyrimidyl)sulfonylurea derivatives, in which the pyridyl or pyrimidyl moiety is substituted ortho- to the sulfonylurea bridge with an electron-withdrawing group, would exhibit high herbicidal activity.

West Germal Patent Application No. 3151450A, published 7/14/83, filed by Celamerck discloses sulfamate sulfonylureas of the following general structure. ##STR2##

European Publication No. 126,711, published 11/28/84 discloses herbicidal sulfonylureas of the formula ##STR3## where, in part, ##STR4## --CH═CH-- or an annelated phenyl ring; Q is, inter alia, halogen, C₁ -C₄ alkyl, nitro, C₁ -C₄ alkoxycarbonyl, C₁ -C₄ alkylsulfonyl; R₂ and R₃ are independently H, halogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, etc.; or

Q and R₂ together can also form a 2-4 membered carbon chain, which may still contain an oxygen or sulfur atom, or the group NR₅ ;

R₁ is H, halogen, nitro or a group ##STR5## COR₉ or --(Y)_(m) --R₁₀ ; R₄ is H, halogen, C₁ -C₄ alkyl, methoxy, nitro or trifluoromethyl;

Z is O or S;

R₅ is H, C₁ -C₄ alkyl or C₃ -C₄ alkenyl.

SUMMARY OF THE INVENTION

This invention pertains to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as preemergent or postemergent herbicides or plant growth regulants. ##STR6## wherein ##STR7## W₁ is O or S; R is H or CH₃ ;

R₁ is NO₂, F, Cl, Br, CF₃, C₁ -C₃ alkyl, C₁ -C₂ alkyl substituted with OCH₃ or OC₂ H₅, CO₂ R₉, SO₂ N(CH₃)R₁₀, S(O)_(n) R₁₁, S(O)_(n) CF₂ H, S(O)_(n) CF₃, OR₁₂, OSO₂ R₁₁, CH₂ CH₂ Cl, C(O)R₂₅, ##STR8## R₂ is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ monohaloalkyl, CF₃ or halogen;

R₃ is Cl, SO₂ CH₃, SO₂ N(CH₃)₂, OCH₃, NO₂ or N(CH₃)₂ ;

R₄ is H or CH₃ ;

R₅ is H or C₁ -C₃ alkyl;

R₆ is CO₂ R₉, S(O)_(n) R₁₁, C₁ -C₃ alkyl, Cl, Br or SO₂ N(CH₃)₂ ;

R₇ is S(O)_(n) R₁₁, OSO₂ R₁₁, C₁ -C₃ alkyl, C₁ -C₃ alkoxy or Cl;

R₈ is C₁ -C₃ alkyl;

R₉ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ;

R₁₀ is C₁ -C₃ alkyl or OCH₃ ;

R₁₁ is C₁ -C₃ alkyl;

R₁₂ is C₁ -C₃ alkyl, CH₂ CH₂ OCH₃, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl or C₁ -C₃ alkyl substituted with 1-3 atoms of Cl or F, or with 1 Br;

R₁₃ is H or CH₃ ;

m is 0 or 1;

n is 0, 1 or 2;

Q is O, S, SO or SO₂ ; ##STR9## W is F, CH₃, OCH₃, CN, CO₂ CH₃, CO₂ C₂ H₅, NO₂, C(O)R₂₅, S(O)R₁₁, SO₂ R₁₁ or CONR₁₄ R₁₅ ;

R₁₄ and R₁₅ are independently H or CH₃ ;

X is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, Cl, CH₂ OH, NHCH₃ or N(CH₃)₂ ;

Y is CH₃, OCH₃, OC₂ H₅ or Cl;

Z is CH or N;

p is 0 or 1;

Q₁ is O, NCH₃ or CH₂ ;

Q₂ is O, NCH₃ or CH₂ ;

Q₃ is O, SO or SO₂ ;

R₁₆ is H, Cl, Br, F, CH₃, OCH₃, SCH₃ or CF₃ ;

R₁₇ is H, C₁ -C₅ alkyl, C₂ -C₃ alkoxycarbonyl, C₁ -C₃ alkyl substituted with 1-3 halogen atoms selected from 0-3 F, 0-3 Cl and 0-1 Br, C₂ -C₄ alkyl substituted with OCH₃, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl or benzyl;

R₁₈ is H or C₁ -C₂ alkyl;

R₁₉ is H, C₁ -C₃ alkyl, CH₂ CH═CH₂ or phenyl;

R₂₀ is C₁ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₉, SO₂ N(CH₃)R₁₀, SO₂ R₁₁, OCF₂ H or phenyl;

R₂₁ is H, Cl or CH₃ ;

R₂₂ is H or C₁ -C₃ alkyl;

R₂₃ and R₂₄ are independently H or Cl; and

R₂₅ is H or C₁ -C₂ alkyl;

and their agriculturally suitable salts; provided that

(1) X and Y cannot simultaneously be Cl;

(2) when either X or Y is Cl, then Z is CH;

(3) when X and Y are both CH₃ and Z is CH, then W is other than NO₂ ;

(4) when Z is N, then Q₃ is SO or SO₂ ; and

(5) when J is J-11, R₁₉ and R₂₀ are not both phenyl.

In the above definitions, the term "alkyl", used eiter alone or in compound words such as "alkylthio" or "haloalkyl", denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl and pentyl isomers.

Alkoxy denotes methoxy, ethoxy, n-propoxy or isopropoxy.

Alkenyl denotes straight chain or branched alkenes, e.g. 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers.

Alkynyl denotes straight chain or branched alkynes, e.g. ethynyl, 1-propynyl, 2-propynyl and the different butynyl isomers.

The term "halogen", either alone or in compound words such as "haloalkyl", denoted fluorine, chlorine, bromine or iodine.

Alkoxycarbonyl denotes methoxycarbonyl or ethoxycarbonyl.

Alkylsulfinyl denotes methylsulfinyl or ethylsulfinyl.

Alkylthio and alkylsulfonyl are defined in an analogous manner.

Preferred for their higher herbicidal activity, greater plant growth regulant activity and/or more favorable ease of synthesis are:

(1) Compounds of Formula I where

R is H; and

W₁ is O;

(2) Compounds of Preferred 1 where A is A-1;

(3) Compounds of Preferred 1 where A is A-2;

(4) Compounds of Preferred 1 where A is A-3;

(5) Compounds of Preferred 1 where A is A-4;

(6) Compounds of Preferred 1 where J is J-1;

(7) Compounds of Preferred 1 where J is J-2;

(8) Compounds of Preferred 1 where J is J-3;

(9) Compounds of Preferred 1 where J is J-4;

(10) Compounds of Preferred 1 where J is J-5;

(11) Compounds of Preferred 1 where J is J-6;

(12) Compounds of Preferred 1 where J is J-7;

(13) Compounds of Preferred 1 where J is J-8;

(14) Compounds of Preferred 1 where J is J-9;

(15) Compounds of Preferred 1 where J is J-10;

(16) Compounds of Preferred 1 where J is J-11;

(17) Compounds of Preferred 1 where J is J-12;

(18) Compounds of Preferred 1 where J is J-13;

(19) Compounds of Preferred 1 where J is J-14;

(20) Compounds of Preferred 1 where J is J-15;

(21) Compounds of Preferred 1 where J is J-16;

(22) Compounds of Preferred 1 where J is J-17;

(23) COmpounds of Preferred 6 where

R₁ is F, Cl, Br, NO₂, CH₃, OCH₃, OC₂ H₅, OCH₂ CH═CH₂, CO₂ CH₃, CO₂ C₂ H₅, CF₃, CH₂ CH₂ OCH₃, SO₂ N(CH₃)₂, SO₂ CH₃, SO₂ C₂ H₅, OSO₂ CH₃ or OSO₂ C₂ H₅ ; and

R₂ is H, F, Cl, CH₃, OCH₃ or SCH₃ ;

(24) Compounds of Preferred 8 where R₁₆ is H;

(25) Compounds of Preferred 9 where R₁₆ is H;

(26) Compounds of Preferred 13 where R₁₆ is H;

(27) Compounds of Preferred 15 where R₂₁ is H;

(28) Compounds of Preferred 16 where R₂₁ is H;

(29) Compounds of Preferred 17 where R₂₁ is H;

(30) Compounds of Preferred 18 where R₂₁ is H;

(31) Compounds of Preferred 21 where R₁₆ is H;

(32) Compounds of Preferred 22 where R₁₆ is H;

(33) Compounds of Preferred 23 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(34) Compounds of Preferred 7 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(35) Compounds of preferred 24 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(36) Compounds of Preferred 25 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(37) Compounds of Preferred 10 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(38) Compounds of Preferred 11 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(39) Compounds of Preferred 12 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(40) Compounds of Preferred 26 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(41) Compounds of Preferred 14 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(42) Compounds of Preferred 27 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(43) Compounds of Preferred 28 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(44) Compounds of Preferred 29 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(45) Compounds of Preferred 30 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(46) Compounds of Preferred 19 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(47) Compounds of Preferred 20 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(48) Compounds of Preferred 31 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(49) Compounds of Preferred 32 where X and Y are independently CH₃ or OCH₃ ; and W is CN, NO₂ or CO₂ CH₃ ;

(50) Compounds of Preferred 33 where A is A-1; and Z is CH;

(51) Compounds of Preferred 34 where A is A-1; and Z is CH;

(52) Compounds of Preferred 35 where A is A-1; and Z is CH;

(53) Compounds of Preferred 36 where A is A-1; and Z is CH;

(54) Compounds of Preferred 37 where A is A-1; and Z is CH;

(55) Compounds of Preferred 38 where A is A-1; and Z is CH;

(56) Compounds of Preferred 39 where A is A-1; and Z is CH;

(57) Compounds of Preferred 40 where A is A-1; and Z is CH;

(58) Compounds of Preferred 41 where A is A-1; and Z is CH;

(59) Compounds of Preferred 42 where A is A-1; and Z is CH;

(60) Compounds of Preferred 43 where A is A-1; and Z is CH;

(61) Compounds of Preferred 44 where A is A-1; and Z is CH;

(62) Compounds of Preferred 45 where A is A-1; and Z is CH;

(63) Compounds of Preferred 46 where A is A-1; and Z is CH;

(64) Compounds of Preferred 47 where A is A-1; and Z is CH;

(65) Compounds of Preferred 48 where A is A-1; and Z is CH;

(66) Compounds of Preferred 49 where A is A-1; and Z is CH;

Specifically preferred for their highest herbicidal activity, greatest plant growth regulant activity and/or most favorable ease of synthesis are:

Methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]aminosulfonyl]benzoate, m.p. 158°-162° C.;

N'-[(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide, m.p. 163°-165° C.;

Methyl 2-[[N-(2,6-dimethoxy-5-nitropyrimidin-4-yl)aminocarbonyl]aminosulfonyl]benzoate, m.p. 150°-152° C.(d); and

Methyl 2-[[(2-dimethylaminosulfonylphenyl)sulfonylamino]carbonylamino]-4,6-dimethylpyridin-3-carboxylate, m.p. 198°-201° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formula I can be prepared by reacting an appropriate aminoheterocycle of Formula II with an appropriately substituted sulfonyl isocyanate or sulfonyl isothiocyanate of Formula III, as shown in in Equation 1.

EQUATION 1 ##STR10## wherein A, J, W₁ and R are as previously defined.

The reaction of Equation 1 is best carried out in inert organic solvents such as methylene chloride, tetrahydrofuran, or acetonitrile, at ambient pressure and temperature. The mode of addition is not critical; however, it is often convenient to add the sulfonyl isocyanate to a stirred suspension or solution of the aminoheterocycle. Since such isocyanates usually are liquids, their additions can be easily controlled.

The reaction is generally exothermic. In some cases, the desired product is insoluble in the warm reaction medium and crystallize from it in pure form. Products soluble in the reaction medium are isolated by evaporation of the solvent, trituration of the solid residue with solvents such as 1-chlorobutane or ethyl ether, and filtration.

The sulfonyl isocyanates III used as starting materials are generally known in the art and can be prepared by known methods. One method involves reacting an appropriate benzene or heterocyclic sulfonamide with phosgene in the presence of an alkyl isocyanate, such as n-butyl isocyanate, and a tertiary amine catalyst, such as 1,4-diazabicyclo[2.2.2]octane, at reflux in a solvent such as xylene or chlorobenzene. See H. Ulrich and A. A. Y. Sayigh, Newer Methods of Preparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, New York and London, W. Foerst Ed.

The sulfonyl isocyanates III can also be prepared from sulfonamides by a two step procedure involving (a) reacting the sulfonamides with an alkyl isocyanate in the presence of a base such as K₂ CO₃ at reflux in an inert solvent such as 2-butanone, forming an alkylsulfonylurea, and (b) reacting this compound with phosgene and tertiary amine catalyst at reflux in xylene solvent.

Sulfonyl isothiocyanates can be prepared according to the methods described by K. Hartke, Arch. Pharm., 299, 174 (1966).

The preparation of sulfonamides from ammonium hydroxide and sulfonyl chlorides is widely reported in the literature, e.g. Crossley et al., J. Am. Chem. Soc., 60, 2223 (1938). Certain sulfonyl chlorides are best prepared by chlorosulfonation of a substituted benzene, naphthalene, or thiophene in carbon tetrachloride according to the teaching of H. T. Clarke et al., Org. Synth., Coll. Vol. 1, 2nd Ed. 1941, p. 85. Other sulfonyl chlorides can be made by diazotization of the appropriate amine with sodium nitrite in HCl, followed by reaction of the diazonium salt with sulfur dioxide and cuprous chloride in acetic acid according to the teachings of H. L. Yale and F. Sowinski, J. Org. Chem. 25, 1824 (1960).

More specifically, the compounds of this invention may be prepared as described above by the route illustrated below. ##STR11##

Reference to the following patents is suggested for further details regarding the preparation of the sulfonyl isocyanates III: U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,238,621 and EP-A-107,979.

Appropriately substituted aminoheterocycles of Formula II, where R=H and A is a substituted 2-pyridyl or 4-pyrimidyl moiety are generally known in the art and are reviewed in The Chemistry of Heterocyclic Compounds, "Pyridine and its Derivatives", Vol. 14, Suppl. Parts I and III (1974), and "The Pyrimidines" (1962) and Suppl. 1 (1970), (John Wiley and Sons, Inc., New York). Commonly used starting materials for the synthesis of such substituted heterocycles are malononitrile, cyanoacetates, cyanoacetamides, ethoxy methylene malononitriles, ammonia, urea, β-diketones, β-ketoesters, malonates, alkylamidines and alkylsulfonaylacetonitriles. Some literature techniques are illustrated below. Using these techniques or suitable modifications that would be apparent to one skilled in the art, the 2-aminopyridine and 4-aminopyrimidine intermediates can be readily prepared.

Condensation of ethoxyethylidenemalononitrile and acetamidine yields the corresponding 4-aminopyrimidine-5-carbonitrile as reported, Chem. Ber., 71, 87 (1938). ##STR12##

The following sequence of reactions is reported [J. Med. Chem., 24, 382 (1981)] to yield chloro and alkoxy substituted 4-aminopyrimidine-5-carbonitriles. ##STR13##

Treatment of methyl cyanoacetate with ethanolic hydrogen chloride affords the imidate which is condensed with acetylacetone as described [Chem. Ber., 73, 542 (1940)] to give the 2-amiopyridine-3-carboxylate. ##STR14##

Heterocyclic amines II in which W is a nitro group are prepared by nitration of the corresponding unsubstituted amine as is reported for 2-amino-4,5-dimethyl-3-nitropyridine, Rocz. Chem., 37, 385 (1963), [Chem. Abstr., 59, 11486 (1963)]. ##STR15##

Those intermediates of Formula II in which A is A-2, A-3 or A-4 may be readily prepared by known methods or modifications of these methods. Reference to the following publications is suggested for further details: Brit. Pat. GB No. 1,057,612, U.S. Pat. No. 3,318,881, Belg. Pat. BE No. 895995A, Japan, Kokai JP No. 48/72197, Japan Kokai JP No. 48/72169, U.S. Pat. No. 4,209,620, T. R. Kasturi et al., Tet. Lett., 21(9) 865-6, and Y. D. Smirnov et al., Zh. Prikl. Khim., 44(12), 2758-9.

Those intermediates of Formula II in which R is a methyl group may be readily prepared from the corresponding aminoheterocycles (R=H) by known methods for the monomethylation of heterocyclic amines; J. Chem. Soc. Perkin I, 1569 (1981).

Agriculturally suitable salts of the compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. Suitable salts include alkali or alkaline earth metal salts, e.g. calcium, potassium or sodium salts; quaternary amine salts; and acid addition salts, e.g., p-toluenesulfonic acid or trichloroacetic acid addition salts.

The following examples teach the preparation of compounds of the this invention in more detail. Unless otherwise indicated, all parts are by weight and temperatures in °C.

EXAMPLE 1 N-[(3-Cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide (I; J=J-1, R₁ =NO₂, R₂ =H; Z=CH, W=CN, X=Y=CH₃, R=H)

To a stirred suspension of 0.5 g (4.3 mmol) 2-amino-4,6-dimethyl-3-pyridinecarbonitrile [Archiv. Pharm., 288, 174 (1955)] in 20 ml of acetonitrile was added 1.3 g (5.7 mmol) o-nitrobenzenesulfonyl isocyanate. The mixture was then heated to reflux (80°) for four hours followed by stirring at ambient temperature overnight. A crystalline product was collected, 0.5 g, m.p. 174°-176° dec. An infrared spectrum (nujol mull) exhibited absorptions at 1700, 1720 and 2240 cm⁻¹ ; and a proton magnetic resonance spectrum (90 MHz NMR) exhibited absorptions at 2.5 (s, 3H), 2.6 (s, 3H), 7.05 (s, H), 7.7 (s br, NH), 7.8 (m, 3H), 8.4 (m, 1H), 9.7 (s br, NH) ppm indicating the title compound.

EXAMPLE 2 2-Chloro-N-[(4,6-dimethyl-3-methoxycarbonylpyridin-2-yl)aminocarbonyl]benzenesulfonamide (I; J=J-1, R₁ =Cl, R₂ =H, Z=CH, W=CO₂ CH₃, X=Y=CH₃, R=H)

A mixture of 0.5 g (2.8 mmol) methyl 2-amino-4,6-dimethylpyridine-3-carboxylate [preparation analogous to ethyl ester: Chem. Ber., 73, 542 (1940)] and 0.78 g (3.6 mmol) o-chlorobenzenesulfonyl isocyanate were combined in 40 ml acetonitrile and stirred at ambient temperature for forty-eight hours. The homogeneous mixture was then evaporated and triturated with n-chlorobutane to afford 1.04 g of product, m.p. 175°-177°. IR (nujol) 1670, 1710 cm⁻¹ ; and NMR (CDCl₃) 2.58 (s, 3H), 2.60 (s, 3H), 3.95 (s, 3H), 6.85 (s, 1H), 7.55 (m, 3H), 8.40 (m, 1H), 10.2 (s br, NH), 14.2 (s br, NH) ppm indicated the title compound.

EXAMPLE 3 2,6-Dimethoxy-5-nitro-4-pyrimidinamine (II; Z=N, W=NO₂, X=Y=OCH₃)

To a solution of 20 ml of concentrated nitric acid and 16 ml of concentrated sulfuric acid was added 3.9 g (0.025 mmol) of 2,6-dimethoxy-4-pyrimidinamine. The resulting solution was stirred at ambient temperature and pressure for thirty minutes and was then stirred at 50° for fifteen minutes. The solution was then cooled in an ice bath to ˜0° C. The solid was collected by filtration, washed with water and dried in an oven at 60° C. to afford 3.6 g of the title compound, m.p. 178°-179° C.

NMR (DMSO-d₆)δ: 3.96 (d, 6H); and 8.2 (broad s, 2H) ppm.

EXAMPLE 4 2-[[(2,6-Dimethoxy-5-nitropyrimidin-4-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester (I; J=J-1, R₁ =CO₂ CH₃, R₂ =H; Z=N, W=NO₂, X=Y=OCH₃, R=H)

A solution of 0.2 g (1.0 mmol) of 2,6-dimethoxy-5-nitro-4-pyrimidinamine and 0.6 g (2.4 mmol) of 2-carbomethoxybenzenesulfonyl isocyanate in 15 ml of methylene chloride was stirred at ambient temperature and pressure for 12 hours under anhydrous conditions. The solvent was then evaporated under reduced pressure. The residue was stirred in n-butyl chloride (70 ml). The solid was then collected by filtration, washed with ether and then dried in an oven to afford 0.4 g of the title compound, m.p. 150°-152° dec.

NMR (DMSO-d₆)δ: 3.9-4.1 (m, 9H, OCH₃); 7.7-8.5 (m, 4H, ArH); and 10-12 (br, 2H, NH) ppm.

EXAMPLE 5 2-Chloro-N-[(5-cyano-2,6-dimethylpyrimidin-4-yl)aminocarbonyl]benzenesulfonamide (I; J=J-1, R₁ =Cl, R₂ =H; Z=N, W=CN, X=Y=CH₃, R=H)

4.35 g of 2-Chlorobenzenesulfonyl isocyanate was dissolved in 10 ml xylenes and 25 ml methylene chloride. To this was added 2.96 g of 4-amino-2,6-dimethyl-5-pyrimidine carbonitrile and a catalytic amount of 1,4-diazabicyclo-[2.2.2]octane. The reaction was stirred under a CaSO₄ drying tube for three days. The reaction was filtered to remove unreacted pyrimidine, and then the desired product was precipitated by addition of 1-chlorobutane, filtered off, rinsed well with 1-chlorobutane and dried in vacuo giving 5.2 g of the desired product, m.p. 125°-127°. IR: 2240 cm⁻¹ (C.tbd.N), 1730 cm⁻¹ (C═O); NMR (DMSO-d₆)δ: 2.6 (s, 6H), 7.4-8.1 (m, 4H) ppm indicating the title compound.

By using techniques analogous to those described in Examples 1 through 5 and/or the processes described above, the compounds of Tables I through II may be prepared.

                                      TABLE I                                      __________________________________________________________________________      ##STR16##                                                                     R.sub.1      R.sub.2                                                                              R  W       X     Y   Z m.p. (°C.)                    __________________________________________________________________________     NO.sub.2     H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               174-176 (d)                          NO.sub.2     H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 154 (d)                              NO.sub.2     H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     NO.sub.2     6-Cl  H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      F            H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     F            H     H  CO.sub.2 CH(CH.sub.3).sub.2                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     F            H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      Cl           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 125-127                              Cl           H     H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N 187-190 (d)                          Cl           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               175-178 (d)                          Cl           H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               175-177 (d)                          Cl           H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N 143-145 (d)                          Cl           5-Cl  H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CF.sub.3     H     H  CN      CH.sub.3                                                                             OCH.sub.3                                                                          CH                                     CF.sub.3     H     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           N                                      Br           H     H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     CH.sub.3     H     H  C(O)NH.sub.2                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.3     5-Cl  H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      -n-C.sub.3 H.sub.7                                                                         H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH.sub.2 OCH.sub.3                                                                          H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 OCH.sub.3                                                                          H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H     H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     SCF.sub.2 H  H     H  SO.sub.2 CH.sub. 3                                                                     CH.sub.3                                                                             CH.sub.3                                                                           N                                      SCF.sub.2 H  H     H  NO.sub.2                                                                               OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     SCF.sub.2 H  5-CH.sub.3                                                                           H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      Cl           H     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               150-152                              CO.sub.2 CH.sub.3                                                                           H     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               150-153                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               165-167                              OSO.sub.2 CH.sub.3                                                                          H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 138 (d)                              OSO.sub.2 CH.sub.3                                                                          H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OSO.sub.2 C.sub.3 H.sub.7 -n                                                                H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      OCF.sub.2 H  H     H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      OCH.sub.3    H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OC.sub.2 H.sub.5                                                                            H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OC.sub.3 H.sub.7 -n                                                                         H     H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      OCH.sub.2 CH.sub.2 OCH.sub.3                                                                H     H  S(O)CH.sub. 3                                                                          CH.sub.3                                                                             CH.sub.3                                                                           CH                                     C.sub.2 H.sub.5                                                                             H     H  CO.sub.2 CH.sub.3                                                                      Cl    CH.sub.3                                                                           CH                                      .sub.-i-C.sub.3 H.sub.7                                                                    H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SCH.sub.3    H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SCH.sub.3    H     CH.sub.3                                                                          NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          CH                                     SC.sub.2 H.sub.5                                                                            H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      SC.sub.3 H.sub.7 -n                                                                         H     H  NO.sub.2                                                                               OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     SO.sub.2 CH.sub.3                                                                           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 196-201                              SO.sub.2 CH.sub.3                                                                           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               230-234 (d)                          SO.sub.2 CH.sub.3                                                                           H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               187-189                              SO.sub.2 CH.sub.3                                                                           H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N 184-185 (d)                          SO.sub.2 CH.sub.3                                                                           H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SO.sub.2 C.sub.3 H.sub.7 -n                                                                 H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SO.sub.2 C.sub.2 H.sub.5                                                                    H     H  NO.sub.2                                                                               CH.sub.3                                                                             OCH.sub.3                                                                          N                                      SO.sub.2 C.sub.3 H.sub.7 -n                                                                 H     H  CN      OCH.sub.3                                                                            OCH.sub.3                                                                          CH                                     CO.sub.2 CH.sub.3                                                                           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 167-168                              CO.sub.2 CH.sub.3                                                                           H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               158-162                              CO.sub.2 CH.sub.3                                                                           H     H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N 170-172                              CO.sub.2 CH.sub.3                                                                           H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               159-161                              CO.sub.2 CH.sub.3                                                                           H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N 150-152                              CO.sub.2 CH.sub.3                                                                           H     H  CN      Cl    CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                           H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           5-Cl  H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                          H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      CO.sub.2 CH.sub.3                                                                           5-F   H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             Cl  CH                                     CO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                           H  S(O)C.sub.2 H.sub.5                                                                    CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           H     H  CONHCH.sub.3                                                                           OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           H     H  CON(CH.sub. 3).sub.2                                                                   CH.sub.3                                                                             CH.sub.3                                                                           N                                      CO.sub.2 CH.sub.3                                                                           H     H  CON(CH.sub.3).sub.2                                                                    Cl    CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           H     CH.sub.3                                                                          CO.sub.2 CH.sub.3                                                                      OC.sub.2 H.sub.5                                                                     CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           H     H  CO.sub.2 CH.sub.3                                                                      Cl    CH.sub.3                                                                           CH                                     CO.sub.2 CH.sub.3                                                                           H     H  CN      CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                           N                                      CO.sub.2 CH.sub.3                                                                           5-Br  H  CN      CH.sub.2 OCH.sub.3                                                                   OCH.sub.3                                                                          CH                                     CO.sub.2 CH.sub.3                                                                           H     H  NO.sub.2                                                                               CH.sub.2 OCH.sub.3                                                                   CH.sub.3                                                                           N                                      CO.sub.2 CH.sub.3                                                                           H     H  NO.sub.2                                                                               OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                                                                   N                                      CO.sub.2 CH.sub.3                                                                           H     H  SO.sub.2 CH.sub.3                                                                      Cl    OCH.sub.3                                                                          CH                                     CO.sub.2 CH.sub.3                                                                           H     H  SO.sub.2 C.sub.2 H.sub.5                                                               OCH.sub.3                                                                            Cl  CH                                     CO.sub.2 C.sub.2 H.sub.5                                                                    H     CH.sub.3                                                                          CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CO.sub.2 C.sub.3 H.sub.7 -n                                                                 H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               148-150                              CO.sub.2 C.sub.2 H.sub.5                                                                    H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CO.sub.2 CH.sub. 2 CHCH.sub.2                                                               H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               134-137                              CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                               H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                        H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      ##STR17##   H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      ##STR18##   H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                       ##STR19##   H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      ##STR20##   H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                       ##STR21##   H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      CO.sub.2 CH.sub.3                                                                           5-Cl  H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               192-195 (d)                          SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N 82                                   SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               163-165                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N 193-195                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                                                               198-201                              SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N 130-131 (d)                          SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                         H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      SO.sub.2 N(CH.sub.3).sub.2                                                                  H     CH.sub.3                                                                          CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      ##STR22##   5-Cl  H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     SO.sub.2 N(CH.sub.3)OCH.sub.3                                                               H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH.sub.2 OCH.sub.2 CH.sub.3                                                                 H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH.sub.2 OCH.sub.2 CH.sub.3                                                                 H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH(CH.sub.3)OCH.sub.3                                                                       H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                          H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      CH(CH.sub.3)OC.sub.2 H.sub.5                                                                H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OCH.sub.2 CHCH.sub.2                                                                        H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OCH.sub.2 CCH                                                                               H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     OCH.sub.2 CHCHCH.sub.3                                                                      H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      OCH.sub.2 CCCH.sub.3                                                                        H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     Cl           H     H  SO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                          N 170-173 (d)                          CO.sub.2 CH.sub.3                                                                           H     H  SO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                          N 180-182 (d)                          SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  SO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            OCH.sub.3                                                                          N 188-190 (d)                          Cl           H     H  S(O)CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                          N 191-193 (d)                          CO.sub.2 CH.sub.3                                                                           H     H  S(O)CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                          N 185-188 (d)                          SO.sub.2 N(CH.sub.3).sub.2                                                                  H     H  S(O)CH.sub.3                                                                           OCH.sub.3                                                                            OCH.sub.3                                                                          N 193-196 (d)                          NO.sub.2     H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           CH                                     NO.sub.2     H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           N                                      NO.sub.2     H     H  OCH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3                                                                           CH                                     NO.sub.2     6-Cl  H  OCH.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                           N                                      F            H     H  CHO     CH.sub.3                                                                             CH.sub.3                                                                           CH                                     F            H     H  C(O)C.sub.2 H.sub.5                                                                    CH.sub.3                                                                             CH.sub.3                                                                           N                                      Cl           H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           N                                      Cl           H     H  F       OCH.sub.3                                                                            CH.sub.3                                                                           N                                      Cl           H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           CH                                     Cl           H     H  OCH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3                                                                           CH                                     Cl           H     H  CH.sub.3                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      Cl           5-Cl  H  CHO     CH.sub.3                                                                             CH.sub.3                                                                           N                                      CF.sub.3     H     H  F       CH.sub.3                                                                             OCH.sub.3                                                                          CH                                     CF.sub.3     H     H  OCH.sub.3                                                                              CH.sub.3                                                                             CH.sub.3                                                                           N                                      Br           H     H  OCH.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     CH.sub.3     H     H  C(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.3     5-Cl  H  F       CH.sub.3                                                                             CH.sub.3                                                                           CH                                      -n-C.sub.3 H.sub.7                                                                         H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH.sub.2 OCH.sub.3                                                                          H     H  F       CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 OCH.sub.3                                                                          H     H  COC.sub.2 H.sub.5                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 H     H  OCH.sub.3                                                                              OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     SCF.sub.2 H  H     H  CHO     CH.sub.3                                                                             CH.sub.3                                                                           N                                      SCF.sub.2 H  H     H  CH.sub.3                                                                               OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     SCF.sub.2 H  5-CH.sub.3                                                                           H  F       OCH.sub.3                                                                            CH.sub.3                                                                           N                                      Cl           H     H  CH.sub.3                                                                               CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CHO          H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     C(O)CH.sub.3 H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      C(O)C.sub.2 H.sub.5                                                                         H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH(OCH.sub.3).sub.2                                                                         6-Cl  H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      CH(OC.sub.2 H.sub.5).sub.2                                                                  H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     1,3-dioxolan-2-yl                                                                           H     H  CO.sub.2 CH(CH.sub.3).sub.2                                                            OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     C(CH.sub.3)(OCH.sub.3).sub.2                                                                H     H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      C(CH.sub.3)(OC.sub.2 H.sub.5).sub.2                                                         H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      1,3-dioxolan-2-methyl-2-yl                                                                  H     H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      C(C.sub.2 H.sub.5)(OCH.sub.3).sub.2                                                         H     H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     C(C.sub.2 H.sub.5)(OC.sub.2 H.sub.5).sub.2                                                  H     H  CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     1,3-dioxolan-2-ethyl-2-yl                                                                   H     H  NO.sub.2                                                                               OCH.sub.3                                                                            OCH.sub.3                                                                          N                                      Cl           OC.sub.2 H.sub.5                                                                     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      S(O)CF.sub.3 H     H  CN      CH.sub.3                                                                             OCH.sub.3                                                                          CH                                     S(O).sub.2 CF.sub.3                                                                         H     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           N                                      SCF.sub.3    H     H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     CH.sub.3     C.sub.2 H.sub.5                                                                      H  C(O)NH.sub.2                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.3     SCH.sub.3                                                                            H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                      -n-C.sub.3 H.sub.7                                                                         S(O)CH.sub.3                                                                         H  CN      CH.sub.3                                                                             CH.sub.3                                                                           CH                                     CH.sub.2 OCH.sub.3                                                                          S(O).sub.2 CH.sub.3                                                                  H  CN      CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub. 2 OCH.sub.3                                                                         CH.sub.2 Cl                                                                          H  S(O)CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                                                           N                                      CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CH.sub.2 CH.sub.2 Cl                                                                 H  CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     S(O)CF.sub.2 H                                                                              H     H  SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                             CH.sub.3                                                                           N                                      S(O)CF.sub.2 H                                                                              H     H  NO.sub.2                                                                               OCH.sub.3                                                                            CH.sub.3                                                                           CH                                     S(O)CF.sub.2 H                                                                              5-CH.sub.3                                                                           H  CN      OCH.sub.3                                                                            CH.sub.3                                                                           N                                      Cl           SC.sub.2 H.sub.5                                                                     H  CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                             CH.sub.3                                                                           CH                                     __________________________________________________________________________

                                      TABLE I-a                                    __________________________________________________________________________      ##STR23##                                                                     R.sub.1 R.sub.2                                                                            R W       X   Y   Z  m.p. (°C.)                             __________________________________________________________________________     NO.sub.2                                                                               H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               NO.sub.2                                                                               H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           N                                                NO.sub.2                                                                               H   H CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               NO.sub.2                                                                               6-Cl                                                                               H CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                          CH.sub.3                                                                           N                                                F       H   H SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               F       H   H CO.sub.2 CH(CH.sub.3).sub.2                                                            OCH.sub.3                                                                          CH.sub.3                                                                           CH                                               F       H   H S(O)CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           N                                                Cl      H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           N                                                Cl      H   H CN      OCH.sub.3                                                                          CH.sub.3                                                                           N                                                Cl      H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               Cl      H   H CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               Cl      H   H NO.sub.2                                                                               OCH.sub.3                                                                          OCH.sub.3                                                                          N                                                Cl      5-Cl                                                                               H SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3                                                                           N                                                CF.sub.3                                                                               H   H CN      CH.sub.3                                                                           OCH.sub.3                                                                          CH                                               CF.sub.3                                                                               H   H CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                           CH.sub.3                                                                           N                                                Br      H   H CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                          CH.sub.3                                                                           CH                                               CH.sub.3                                                                               H   H C(O)NH.sub.2                                                                           CH.sub.3                                                                           CH.sub.3                                                                           N                                                CH.sub.3                                                                               5-Cl                                                                               H CN      CH.sub.3                                                                           CH.sub.3                                                                           CH                                                -n-C.sub.3 H.sub.7                                                                    H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           CH                                               CH.sub.2 OCH.sub.3                                                                     H   H CN      CH.sub.3                                                                           CH.sub.3                                                                           N                                                CH.sub.2 OCH.sub.3                                                                     H   H S(O)CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           N                                                CH.sub.2 CH.sub.2 OCH.sub.3                                                            H   H CO.sub.2 CH.sub.3                                                                      OCH.sub.3                                                                          CH.sub.3                                                                           CH                                               SCF.sub.2 H                                                                            H   H SO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3                                                                           N                                                SCF.sub.2 H                                                                            H   H NO.sub.2                                                                               OCH.sub.3                                                                          CH.sub.3                                                                           CH                                               SCF.sub.2 H                                                                            5-CH.sub.3                                                                         H CN      OCH.sub. 3                                                                         CH.sub.3                                                                           N                                                Cl      H   H CO.sub.2 C.sub.2 H.sub.5                                                               CH.sub.3                                                                           CH.sub.3                                                                           CH                                               __________________________________________________________________________

                  TABLE II-a                                                       ______________________________________                                          ##STR24##                                                                     wherein J-2 is as defined above                                                                                             m.p.                              J   R     R.sub.3    W      X     Y     Z    (°C.)                      ______________________________________                                         J-2 H     Cl         CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                      J-2 H     Cl         CN     CH.sub.3                                                                             CH.sub.3                                                                             CH   178-                                                                           180(d)                            J-2 H     SO.sub.2 CH.sub.3                                                                         CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                     J-2 H     SO.sub.2 N(CH.sub.3).sub.2                                                                NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                      J-2 H     SO.sub.2 CH.sub.3                                                                         SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                      J-2 H     SO.sub.2 N(CH.sub.3).sub.2                                                                CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                      ______________________________________                                    

                                      TABLE II-b                                   __________________________________________________________________________      ##STR25##                                                                     wherein J-3 is as defined above, m is 0 unless                                 indicated by *, wherein m is 1, and R.sub.16 is H.                             J  R  R.sub.4                                                                           R.sub.5                                                                            Q  W    X   Y   Z  m.p. (°C.)                              __________________________________________________________________________     J-3                                                                               H  H  H   O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CN                                                J-3                                                                               H  H  CH.sub.3                                                                           O  CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3                                                                               H  CH.sub.3                                                                          CH.sub.3                                                                           O  CN   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3                                                                               H  CH.sub.3                                                                          CH.sub.3                                                                           S  CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3                                                                               H  H  H   S  CN   OCH.sub.3                                                                          CH.sub.3                                                                           N                                                 J-3                                                                               H  H  CH.sub.3                                                                           S  CN   OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                                J-3                                                                               H  CH.sub.3                                                                          CH.sub.3                                                                           SO.sub.2                                                                          CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3                                                                               H  CH.sub.3                                                                          H   SO.sub.2                                                                          CN   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3                                                                               H  CH.sub.3                                                                          H   SO.sub.2                                                                          NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N                                                 J-3                                                                               H  H  C.sub.3 H.sub.7                                                                    SO.sub.2                                                                          CN   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3                                                                               H  CH.sub.3                                                                          H   O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CH 180-183                                        J-3                                                                               H  CH.sub.3                                                                          CH.sub.3                                                                           O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CH 185-187                                        J-3*                                                                              H  H  H   O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3*                                                                              H  H  CH.sub.3                                                                           O  CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3*                                                                              H  CH.sub.3                                                                          CH.sub.3                                                                           O  CN   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3*                                                                              H  CH.sub.3                                                                          CH.sub.3                                                                           S  CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3*                                                                              H  H  H   S  CN   OCH.sub.3                                                                          CH.sub.3                                                                           N                                                 J-3*                                                                              H  H  CH.sub.3                                                                           S  CN   OCH.sub.3                                                                          OCH.sub.3                                                                          CH                                                J-3*                                                                              H  CH.sub.3                                                                          CH.sub.3                                                                           SO.sub.2                                                                          CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3*                                                                              H  CH.sub.3                                                                          H   SO.sub.2                                                                          CN   CH.sub.3                                                                           CH.sub.3                                                                           N                                                 J-3*                                                                              H  CH.sub.3                                                                          H   SO.sub.2                                                                          NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N                                                 J-3*                                                                              H  H  C.sub.3 H.sub.7                                                                    SO.sub.2                                                                          CN   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3*                                                                              H  CH.sub.3                                                                          H   O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                J-3*                                                                              H  CH.sub.3                                                                          CH.sub.3                                                                           O  CN   CH.sub.3                                                                           CH.sub.3                                                                           CH                                                __________________________________________________________________________

                  TABLE II-c                                                       ______________________________________                                          ##STR26##                                                                     wherein J-4 is as defined above, m is 0 unless                                 indicated by *, wherein m is 1 and R.sub.16 is H.                                                                          m.p.                               J    R.sub.17     W        X     Y     Z    (°C.)                       ______________________________________                                         J-4   -n-C.sub.4 H.sub.9                                                                         CN       CH.sub.3                                                                             CH.sub.3                                                                             CH                                      J-4   -n-C.sub.4 H.sub.9                                                                         CO.sub.2 CH.sub.3                                                                       CH.sub.3                                                                             CH.sub.3                                                                             N                                       J-4  CH.sub.2 CH.sub.2 F                                                                         NO.sub.2 OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                      J-4  CH.sub.2 CH.sub.2 OCH.sub.3                                                                 CN       CH.sub.3                                                                             CH.sub.3                                                                             N                                       J-4  CO.sub.2 C.sub.2 H.sub.5                                                                    CO.sub.2 CH.sub.3                                                                       CH.sub.3                                                                             CH.sub.3                                                                             CH                                      J-4*  -n-C.sub.4 H.sub.9                                                                         CN       CH.sub.3                                                                             CH.sub.3                                                                             CH                                      J-4* CH.sub.3     CO.sub.2 CH.sub.3                                                                       CH.sub.3                                                                             CH.sub.3                                                                             N                                       J-4* H            NO.sub.2 OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                      J-4* CH.sub.2 CH.sub.3                                                                           CN       CH.sub.3                                                                             CH.sub.3                                                                             N                                       J-4* CH.sub.2 CH.sub.2 CH.sub.3                                                                  CO.sub.2 CH.sub.3                                                                       CH.sub.3                                                                             CH.sub.3                                                                             CH                                      ______________________________________                                    

                  TABLE II-d                                                       ______________________________________                                          ##STR27##                                                                     wherein J-5 and J-6 are as defined above                                                                                m.p.                                  J    R     R.sub.6    W      X     Y     Z(°C.)                         ______________________________________                                         J-5  H     CO.sub.2 CH.sub.3                                                                         CN     CH.sub.3                                                                             CH.sub.3                                                                             CH196-                                J-5  H     CO.sub.2 CH.sub.3                                                                         CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH200(d)                              J-6  H     Br         CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-5  H     Br         SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-5  H     Cl         CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                     J-6  H     SO.sub.2 CH.sub.3                                                                         NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     J-5  H     SCH.sub.3  CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                                                                            N                                     J-5  H     SO.sub.2 C.sub.3 H.sub.7 -n                                                               CN     CH.sub.3                                                                             CH.sub.3                                                                             CN                                    J-5  H     CO.sub.2 C.sub.3 H.sub.7  .sub.-i                                                         CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-6  H     CO.sub.2 CH.sub.3                                                                         CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-6  H     CO.sub.2 CH.sub.3                                                                         CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    ______________________________________                                    

                  TABLE II-e                                                       ______________________________________                                          ##STR28##                                                                     wherein J-7 is as defined above                                                                                              m.p.                             J    R     R.sub.7     W      X     Y     Z   (°C.)                     ______________________________________                                         J-7  H     CH.sub.3    CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                   J-7  H     C.sub.2 H.sub.7 -n                                                                         CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                    J-7  H     OCH.sub.3   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                   J-7  H     OC.sub.3 H.sub.7 .sub.-i                                                                   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                    J-7  H     SO.sub.2 CH.sub.3                                                                          SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                    J-7  H     SC.sub.2 H.sub.5                                                                           NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                    J-7  H     OSO.sub.2 C.sub.3 H.sub.7 -n                                                               CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                   J-7  H     Cl          CN     OCH.sub.3                                                                            CH.sub.3                                                                             CH                                   J-7  H     Cl          CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                   ______________________________________                                    

                  TABLE II-f                                                       ______________________________________                                          ##STR29##                                                                     wherein J-8 is as defined above                                                                                               m.p.                            J   R     m     W      X     Y     Z    R.sub.16 R.sub.18                                                                     (°C.)                    ______________________________________                                         J-8 H     0     CN     CH.sub.3                                                                             CH.sub.3                                                                             CH   HH                                     J-8 H     0     CN     CH.sub.3                                                                             CH.sub.3                                                                             N    HH                                     J-8 H     0     CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N    HH                                     J-8 H     0     CN     OCH.sub.3                                                                            CH.sub.3                                                                             N    HH                                     J-8 H     0     NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            CH   HH                                     J-8 H     1     NO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                             N    HH                                     J-8 H     1     CN     CH.sub.3                                                                             CH.sub.3                                                                             CH   HCH.sub.3                              J-8 H     1     CN     OCH.sub.3                                                                            CH.sub.3                                                                             N    HCH.sub.3                              J-8 H     1     SO.sub.2 CH.sub.3                                                                     OCH.sub.3                                                                            CH.sub.3                                                                             CH   HH                                     J-8 H     1     CN     CH.sub.3                                                                             CH.sub.3                                                                             CH   HH     212-                                                                           215(d)                          J-8 H     1     SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N    HH                                     J-8 H     1     NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N    HH                                     J-8 H     1     NO.sub.2                                                                              Cl    OCH.sub.3                                                                            CH   HH                                     J-8 H     1     CN     CH.sub.3                                                                             CH.sub.3                                                                             N    HH                                     J-8 H     1     CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH   HH                                     ______________________________________                                    

                  TABLE II-q                                                       ______________________________________                                          ##STR30##                                                                     wherein J-9 is as defined above                                                                                             m.p.                              J   R     R.sub.8    W      X     Y     Z    (°C.)                      ______________________________________                                         J-9 H     CH.sub.3   CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                     J-9 H     CH.sub.3   CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                      J-9 H     C.sub.2 H.sub.5                                                                           CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                     J-9 H     CH.sub.3   CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                      J-9 H     CH.sub.3   NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                      J-9 H     CH.sub.2 CH.sub.2 CH.sub.3                                                                CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                     J-9 H     CH.sub.3   CN     CH.sub.3                                                                             OCH.sub.3                                                                            CH                                     ______________________________________                                    

                                      TABLE II-h                                   __________________________________________________________________________      ##STR31##                                                                     wherein J-10 is as defined above                                                                                  m.p.                                        J  R R.sub.20                                                                              W    X   Y   Z  R.sub.19                                                                           R.sub.21                                                                          (°C.)                                __________________________________________________________________________     J-10                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-10                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-10                                                                              H Br     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-10                                                                              H Br     SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           Cl                                             J-10                                                                              H Cl     CN   OCH.sub.3                                                                          CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-10                                                                              H SO.sub.2 CH.sub.3                                                                     NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N  CH.sub.3                                                                           H                                              J-10                                                                              H OCF.sub.2 H                                                                           CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           OCH.sub.3                                                                          N  CH.sub.3                                                                           CH.sub.3                                       J-10                                                                              H SO.sub.2 C.sub.3 H.sub.7 -n                                                           CN   CH.sub.3                                                                           CH.sub.3                                                                           CH C.sub.2 H.sub.5                                                                    H                                              J-10                                                                              H CO.sub.2 C.sub.3 H.sub.7 .sub.-i                                                      CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-10                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-10                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH phenyl                                                                             H                                              __________________________________________________________________________

                                      TABLE II-i                                   __________________________________________________________________________      ##STR32##                                                                     wherein J-11 is as defined above                                                                                  m.p.                                        J  R R.sub.20                                                                              W    X   Y   Z  R.sub.19                                                                           R.sub.21                                                                          (°C.)                                __________________________________________________________________________     J-11                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-11                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-11                                                                              H Br     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-11                                                                              H Br     SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           Cl                                             J-11                                                                              H Cl     CN   OCH.sub.3                                                                          CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-11                                                                              H SO.sub.2 CH.sub.3                                                                     NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N  CH.sub.3                                                                           H                                              J-11                                                                              H OCF.sub.2 H                                                                           CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           OCH.sub.3                                                                          N  CH.sub.3                                                                           CH.sub.3                                       J-11                                                                              H SO.sub.2 C.sub.3 H.sub.7 -n                                                           CN   CH.sub.3                                                                           CH.sub.3                                                                           CH C.sub.2 H.sub.5                                                                    H                                              J-11                                                                              H CO.sub.2 C.sub.3 H.sub.7 .sub.-i                                                      CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-11                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-11                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH phenyl                                                                             H                                              __________________________________________________________________________

                                      TABLE II-j                                   __________________________________________________________________________      ##STR33##                                                                     wherein J-12 is as defined above                                                                                  m.p.                                        J  R R.sub.20                                                                              W    X   Y   Z  R.sub.19                                                                           R.sub.21                                                                          (°C.)                                __________________________________________________________________________     J-10                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-12                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-12                                                                              H Br     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-12                                                                              H Br     SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           Cl                                             J-12                                                                              H Cl     CN   OCH.sub.3                                                                          CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-12                                                                              H SO.sub.2 CH.sub.3                                                                     NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N  CH.sub.3                                                                           H                                              J-12                                                                              H OCF.sub.2 H                                                                           CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           OCH.sub.3                                                                          N  CH.sub.3                                                                           CH.sub.3                                       J-12                                                                              H SO.sub.2 C.sub.3 H.sub.7 -n                                                           CN   CH.sub.3                                                                           CH.sub.3                                                                           CH C.sub.2 H.sub.5                                                                    H                                              J-12                                                                              H CO.sub.2 C.sub.3 H.sub.7 .sub.-i                                                      CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                              J-12                                                                              H CO.sub.2 CH.sub.3                                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                              J-12                                                                              H CO.sub.2 CH.sub.3                                                                     CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH phenyl                                                                             H                                              __________________________________________________________________________

                                      TABLE II-k                                   __________________________________________________________________________      ##STR34##                                                                     wherein J-13 is as defined above                                                                                 m.p.                                         J  R R.sub.20                                                                             W    X   Y   Z  R.sub.19                                                                           R.sub.21                                                                          (°C.)                                 __________________________________________________________________________     J-13                                                                              H CO.sub.2 CH.sub.3                                                                    CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                               J-13                                                                              H CO.sub.2 CH.sub.3                                                                    CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                               J-13                                                                              H Br    CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                               J-13                                                                              H Br    SO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           Cl                                              J-13                                                                              H Cl    CN   OCH.sub.3                                                                          CH.sub.3                                                                           N  CH.sub.3                                                                           H                                               J-13                                                                              H SO.sub.2 CH.sub.3                                                                    NO.sub.2                                                                            OCH.sub.3                                                                          OCH.sub.3                                                                          N  CH.sub.3                                                                           H                                               J-13                                                                              H OCF.sub.2 H                                                                          CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           OCH.sub.3                                                                          N  CH.sub.3                                                                           CH.sub. 3                                       J-13                                                                              H SO.sub.2 C.sub.3 H.sub.7 -n                                                          CN   CH.sub.3                                                                           CH.sub.3                                                                           CH C.sub.2 H.sub.5                                                                    H                                               J-13                                                                              H CO.sub.2 C.sub.3 H.sub.7 .sub.-i                                                     CN   CH.sub.3                                                                           CH.sub.3                                                                           CH CH.sub.3                                                                           H                                               J-13                                                                              H CO.sub.2 CH.sub.3                                                                    CN   CH.sub.3                                                                           CH.sub.3                                                                           N  CH.sub.3                                                                           H                                               J-13                                                                              H CO.sub.2 CH.sub.3                                                                    CO.sub.2 CH.sub.3                                                                   CH.sub.3                                                                           CH.sub.3                                                                           CH phenyl                                                                             H                                               __________________________________________________________________________

                  TABLE II-l                                                       ______________________________________                                          ##STR35##                                                                     wherein J-14 is as defined above                                                                                             m.p.                             J    R     R.sub.6    W      X     Y     Z    (°C.)                     ______________________________________                                         J-14 H     CO.sub.2 CH.sub.3                                                                         CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-14 H     CO.sub.2 CH.sub.3                                                                         CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-14 H     Br         SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-14 H     Cl         CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                     J-14 H     SCH.sub.3  CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             OCH.sub.3                                                                            N                                     J-14 H     SO.sub.2 C.sub.3 H.sub.7 -n                                                               CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-14 H     CO.sub.2 C.sub.3 H.sub.7 .sub.-i                                                          CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    ______________________________________                                    

                  TABLE II-m                                                       ______________________________________                                          ##STR36##                                                                     wherein J-15 is as defined above                                                                                             m.p.                             J    R     R.sup.3    W      X     Y     Z    (°C.)                     ______________________________________                                         J-15 H     Cl         CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-15 H     Cl         CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-15 H     SO.sub.2 CH.sub.3                                                                         CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                    J-15 H     SO.sub.2 N(CH.sub.3).sub.2                                                                NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                     J-15 H     SO.sub.2 CH.sub.3                                                                         SO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                     J-15 H     SO.sub.2 N(CH.sub.3).sub.2                                                                CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                     ______________________________________                                    

                  TABLE II-n                                                       ______________________________________                                          ##STR37##                                                                     wherein J-16 is as defined above, m is 0 unless indicated by *,                wherein m is 1, R.sub.16 is H and R.sub.22 is CH.sub.3.                        J     R     W         X     Y      Z    m.p. (°C.)                      ______________________________________                                         J-16  H     CN        CH.sub.3                                                                             CH.sub.3                                                                              CH                                          J-16  H     CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                             CH.sub.3                                                                              N                                           J-16  H     NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                          J-16  H     CN        CH.sub.3                                                                             CH.sub.3                                                                              N                                           J-16  H     CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                             CH.sub.3                                                                              CH                                          J-16* H     CN        CH.sub.3                                                                             CH.sub.3                                                                              CH                                          J-16* H     CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                             CH.sub.3                                                                              N                                           J-16* H     NO.sub.2  OCH.sub.3                                                                            OCH.sub.3                                                                             CH                                          J-16* H     CN        CH.sub.3                                                                             CH.sub.3                                                                              N                                           J-16* H     CO.sub.2 CH.sub.3                                                                        CH.sub.3                                                                             CH.sub.3                                                                              CH                                          ______________________________________                                    

                  TABLE II-o                                                       ______________________________________                                          ##STR38##                                                                     wherein J-17 is as defined above, m is 0 unless                                indicated by *, wherein m is 1 and R.sub.16 is H.                                                                              m.p.                           J    R      R.sub.23                                                                              R.sub.24                                                                            W      X     Y     Z    (°C.)                   ______________________________________                                         J-17 H      H      H    CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17 H      H      Cl   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17 H      Cl     Cl   CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17 H      Cl     Cl   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17 H      H      H    CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                   J-17 H      H      Cl   CN     OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  J-17 H      Cl     H    CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17 H      Cl     H    NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                   J-17 H      Cl     H    CN     CH.sub. 3                                                                            CH.sub.3                                                                             CH                                  J-17 H      Cl     Cl   CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17*                                                                               H      H      H    CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17*                                                                               H      H      Cl   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17*                                                                               H      Cl     Cl   CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17*                                                                               H      Cl     Cl   CO.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17*                                                                               H      H      H    CN     OCH.sub.3                                                                            CH.sub.3                                                                             N                                   J-17*                                                                               H      H      Cl   CN     OCH.sub.3                                                                            OCH.sub.3                                                                            CH                                  J-17*                                                                               H      Cl     H    CN     CH.sub.3                                                                             CH.sub.3                                                                             N                                   J-17*                                                                               H      Cl     H    NO.sub.2                                                                              OCH.sub.3                                                                            OCH.sub.3                                                                            N                                   J-17*                                                                               H      Cl     H    CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  J-17*                                                                               H      Cl     Cl   CN     CH.sub.3                                                                             CH.sub.3                                                                             CH                                  ______________________________________                                    

                  TABLE III-a                                                      ______________________________________                                          ##STR39##                                                                                                                   m.p.                             R.sub.1  R.sub.2  R      Q.sub.1                                                                              p   Y     Z    (°C.)                     ______________________________________                                         NO.sub.2 H        H      O     0   CH.sub.3                                                                             CH                                    NO.sub.2 H        H      O     0   CH.sub.3                                                                             N                                     NO.sub.2 H        H      NCH.sub.3                                                                            0   CH.sub.3                                                                             CH                                    NO.sub.2 5-Cl     H      NCH.sub.3                                                                            1   CH.sub.3                                                                             N                                     CO.sub.2 CH.sub.3                                                                       H        H      CH.sub.2                                                                             0   CH.sub.3                                                                             CH                                    CO.sub.2 CH.sub.3                                                                       H        CH.sub.3                                                                              CH.sub.2                                                                             0   CH.sub.3                                                                             N                                     Cl       H        H      O     0   CH.sub.3                                                                             N                                     Cl       H        H      O     1   CH.sub.3                                                                             N                                     Cl       H        H      O     0   CH.sub.3                                                                             CH                                    Cl       H        H      NCH.sub.3                                                                            0   CH.sub.3                                                                             CH                                    CO.sub.2 CH.sub.3                                                                       5-OCH.sub.3                                                                             H      O     1   OCH.sub.3                                                                            N                                     Cl       5-Cl     H      CH.sub.2                                                                             0   CH.sub.3                                                                             N                                     SO.sub.2 N(CH.sub.3).sub.2                                                              H        H      O     0   OCH.sub.3                                                                            CH                                    CF.sub.3 H        H      NCH.sub.3                                                                            0   CH.sub.3                                                                             N                                     CO.sub.2 CH.sub.3                                                                       H        H      NCH.sub.3                                                                            1   CH.sub.3                                                                             CH                                    CH.sub.3 5-Cl     H      O     0   CH.sub.3                                                                             CH                                    CO.sub.2 C.sub.2 H.sub.5                                                                H        H      O     0   CH.sub.3                                                                             CH                                    CH.sub.2 OCH.sub.3                                                                      H        H      O     0   CH.sub.3                                                                             N                                     CH.sub.2 OCH.sub.3                                                                      H        H      CH.sub.2                                                                             0   CH.sub.3                                                                             N                                     SO.sub.2 CH.sub.3                                                                       H        H      NCH.sub.3                                                                            1   CH.sub.3                                                                             CH                                    SCF.sub.2 H                                                                             H        H      CH.sub.2                                                                             0   CH.sub.3                                                                             N                                     OCH.sub.2 CH.sub.3                                                                      H        H      O     1   CH.sub.3                                                                             CH                                    SCF.sub.2 H                                                                             5-CH.sub.3                                                                              H      O     1   CH.sub.3                                                                             N                                     SO.sub.2 N(CH.sub.3).sub.2                                                              H        H      NCH.sub.3                                                                            0   CH.sub.3                                                                             CH                                    ______________________________________                                    

                  TABLE III-b                                                      ______________________________________                                          ##STR40##                                                                     R.sub.1  R.sub.2  R      Q.sub.1                                                                              p    Y    m.p. (°C.)                     ______________________________________                                         NO.sub.2 H        H      O     0    CH.sub.3                                   NO.sub.2 H        H      O     0    OCH.sub.3                                  NO.sub.2 H        H      NCH.sub.3                                                                            0    CH.sub.3                                   NO.sub.2 5-Cl     H      NCH.sub.3                                                                            1    CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       H        H      CH.sub.2                                                                             0    CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       H        CH.sub.3                                                                              CH.sub.2                                                                             0    CH.sub.3                                   Cl       H        H      O     0    CH.sub.3                                   Cl       H        H      O     1    CH.sub.3                                   Cl       H        H      O     0    CH.sub.3                                   Cl       H        H      NCH.sub.3                                                                            0    CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       5-OCH.sub. 3                                                                            H      O     1    OCH.sub.3                                  Cl       5-Cl     H      CH.sub.2                                                                             0    CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                              H        H      O     0    OCH.sub.3                                  CF.sub.3 H        H      NCH.sub.3                                                                            0    CH.sub.3                                   CO.sub.2 CH.sub.3                                                                       H        H      NCH.sub.3                                                                            1    CH.sub.3                                   CH.sub.3 5-Cl     H      O     0    CH.sub.3                                   CO.sub.2 C.sub.2 H.sub.5                                                                H        H      O     0    CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                      H        H      O     0    CH.sub.3                                   CH.sub.2 OCH.sub.3                                                                      H        H      CH.sub.2                                                                             0    CH.sub.3                                   SO.sub.2 CH.sub.3                                                                       H        H      NCH.sub.3                                                                            1    CH.sub.3                                   SCF.sub.2 H                                                                             H        H      CH.sub.2                                                                             0    CH.sub.3                                   OCH.sub.2 CH.sub.3                                                                      H        H      O     1    CH.sub.3                                   SCF.sub.2 H                                                                             5-CH.sub.3                                                                              H      O     1    CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.2                                                              H        H      NCH.sub.3                                                                            0    CH.sub.3                                   ______________________________________                                    

                  TABLE III-c                                                      ______________________________________                                          ##STR41##                                                                                                                  m.p.                              R.sub.1  R.sub.2  R      Q.sub.3                                                                             p   Y     Z    (°C.)                      ______________________________________                                         NO.sub.2 H        H      O    0   CH.sub.3                                                                             CH                                     NO.sub.2 H        H      SO   0   CH.sub.3                                                                             CH                                     CO.sub.2 CH.sub.3                                                                       5-OCH.sub.3                                                                             H      SO   1   CH.sub.3                                                                             N                                      CO.sub.2 CH.sub.3                                                                       H        H      SO.sub.2                                                                            0   CH.sub.3                                                                             CH                                     CO.sub.2 CH.sub.3                                                                       H        CH.sub.3                                                                              SO.sub.2                                                                            0   CH.sub.3                                                                             N                                      Cl       H        H      O    0   CH.sub.3                                                                             CH                                     Cl       H        H      SO   0   CH.sub.3                                                                             CH                                     Cl       5-Cl     H      SO.sub.2                                                                            0   CH.sub.3                                                                             N                                      SO.sub.2 N(CH.sub.3).sub.2                                                              H        H      O    0   OCH.sub.3                                                                            CH                                     CF.sub.3 H        CH.sub.3                                                                              SO   0   CH.sub.3                                                                             N                                      CO.sub.2 CH.sub.3                                                                       H        H      SO   1   CH.sub.3                                                                             CH                                     CO.sub.2 CH.sub.3                                                                       5-CH.sub.3                                                                              H      O    0   CH.sub.3                                                                             CH                                     CO.sub.2 C.sub.2 H.sub.5                                                                H        H      O    0   CH.sub.3                                                                             CH                                     CH.sub.2 OCH.sub.3                                                                      H        CH.sub.3                                                                              SO.sub.2                                                                            0   CH.sub.3                                                                             N                                      SO.sub.2 CH.sub.3                                                                       H        H      SO   1   CH.sub.3                                                                             CH                                     OCH.sub.2 CH.sub.3                                                                      H        H      SO.sub.2                                                                            0   CH.sub.3                                                                             N                                      SCF.sub.2 H                                                                             H        CH.sub.3                                                                              O    1   CH.sub.3                                                                             CH                                     SO.sub.2 N(CH.sub.3).sub.2                                                              H        CH.sub.3                                                                              SO   0   CH.sub.3                                                                             CH                                     ______________________________________                                    

                                      TABLE III-d                                  __________________________________________________________________________      ##STR42##                                                                     J                         p  Q.sub.1                                                                             Y   Z  m.p. (°C.)                     __________________________________________________________________________     J-2 (R.sub.3 =Cl)         0  O    CH.sub.3                                                                           CH                                       J-3 (Q=O, R.sub.4 =R.sub.5 =H, m=1, R.sub.16 =H)                                                         0  O    CH.sub.3                                                                           CH                                       J-3 (Q=SO.sub.2, R.sub.4 =CH.sub.3, R.sub.5 =H, m=0, R.sub.16 =H)                                        0  O    CH.sub.3                                                                           CH                                       J-3 (Q=SO.sub.2, R.sub.4 =R.sub.5 =CH.sub.3, m=0, R.sub.16 =H)                                           0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =CH.sub.3, m=0, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 = -n-C.sub. 4 H.sub.9, m=0, R.sub.16 =H)                                                   0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      1  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  O    CH.sub.3                                                                           N                                        J-5 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           N                                        J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         1  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-7 (R.sub.7 =Cl)         0  O    CH.sub.3                                                                           CH                                       J-8 (m=0, R.sub.16 =H)    0  O    CH.sub.3                                                                           CH                                       J-8 (m=0, R.sub.16 =H)    0  O    CH.sub.3                                                                           N                                        J-8 (m=1, R.sub.18 =CH.sub.3, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-9 (R.sub.8 =CH.sub.3)   0  O    CH.sub.3                                                                           CH                                       J-10                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-10                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =Br, R.sub.21 =H)                                                      0  O    CH.sub.3                                                                           CH                                       J-11                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-12                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-13                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-14                                                                               (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-15                                                                               (R.sub.3 =SO.sub.2 CH.sub.3)                                                                         0  O    CH  CH                                       J-16                                                                               (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-16                                                                               (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                               1  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                            0  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                            1  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                            0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =Cl, R.sub.16 =H)                                                           0  O    CH.sub.3                                                                           CH                                       __________________________________________________________________________

                  TABLE III-e                                                      ______________________________________                                          ##STR43##                                                                                                           m.p.                                     J                     p  Q.sub.2                                                                              Y      (°C.)                             ______________________________________                                         J-2  (R.sub.3 =Cl)    0  O     CH.sub.3                                        J-3  (Q=O, R.sub.4 =R.sub.5 =H, m=1, R.sub.16 =H)                                                    0  O     CH.sub.3                                        J-3  (Q=SO.sub.2, R.sub.4 =CH.sub.3, R.sub.5 =H, m=0,                                                0  O     CH.sub.3                                        R.sub.16 =H)                                                                   J-3  (Q=SO.sub.2, R.sub.4 =R.sub.5 =CH.sub.3, m=0,                                                   0  O     CH.sub.3                                        R.sub.16 =H)                                                                   J-4  (R.sub.17 =H, m=0, R.sub.16 =H)                                                                 0  O     CH.sub.3                                        J-4  (R.sub.17 =CH.sub.3, m=0, R.sub.16 =H)                                                          0  O     CH.sub.3                                        J-4  (R.sub.17 = -n-C.sub.4 H.sub.9, m=0, R.sub.16 = H)                                              0  O     CH.sub.3                                        J-4  (R.sub.17 =H, m=0, R.sub.16 =H)                                                                 1  O     CH.sub.3                                        J-4  (R.sub.17 =H, m=0, R.sub.16 =H)                                                                 0  NCH.sub.3                                                                            CH.sub.3                                        J-4  (R.sub.17 =H, m=0, R.sub.16 =H)                                                                 0  O     CH.sub.3                                        J-5  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                    0  O     CH.sub.3                                        J-6  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                    0  O     CH.sub.3                                        J-6  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                    0  O     CH.sub.3                                        J-6  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                    1  O     CH.sub.3                                        J-6  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                    0  NCH.sub.3                                                                            CH.sub.3                                        J-7  (R.sub.7 =Cl)    0  O     CH.sub.3                                        J-8  (m=0, R.sub.16 =H)                                                                              0  O     CH.sub.3                                        J-8  (m=0, R.sub.16 =H)                                                                              0  O     CH.sub.3                                        J-8  (m=1, R.sub.18 =CH.sub.3, R.sub.16 =H)                                                          0  O     CH.sub.3                                        J-9  (R.sub.8 =CH.sub.3)                                                                             0   O    CH.sub.3                                        J-10  (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3,                                              0  Ob.21 =H)                                                                            CH.sub.3                                        J-10  (R.sub.19 =CH.sub.3, R.sub.20 =Br, R.sub.21 =H)                                                0  O     CH.sub.3                                        J-11  (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3,                                              0  Ob.21 =H)                                                                            CH.sub.3                                        J-12  (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3,                                              0  Ob.21 =H)                                                                            CH.sub.3                                        J-13  (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3,                                              0  Ob.21 =H)                                                                            CH.sub.3                                        J-14  (R.sub.6 =CO.sub.2 CH.sub.3)                                                                   0  O     CH.sub.3                                        J-15  (R.sub.3 =SO.sub.2 CH.sub.3)                                                                   0  O     CH                                              J-16  (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                         0  O     CH.sub.3                                        J-16  (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                         1  O     CH.sub.3                                        J-17  (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                      0  O     CH.sub.3                                        J-17  (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                      1  O     CH.sub.3                                        J-17  (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                      0  NCH.sub.3                                                                            CH.sub.3                                        J-17  (m=0, R.sub.23 =R.sub.24 =Cl, R.sub.16 =H)                                                     0  O     CH.sub.3                                        ______________________________________                                    

                                      TABLE III-f                                  __________________________________________________________________________      ##STR44##                                                                     J                         p  Q.sub.3                                                                             Y   Z  m.p. (°C.)                     __________________________________________________________________________     J-2 (R.sub.3 =Cl)         0  O    CH.sub.3                                                                           CH                                       J-3 (Q=O, R.sub.4 =R.sub.5 =H, m=1, R.sub.16 =H)                                                         0  O    CH.sub.3                                                                           CH                                       J-3 (Q=SO.sub.2, R.sub.4 =CH.sub.3, R.sub.5 =H, m=0, R.sub.16 =H)                                        0  O    CH.sub.3                                                                           CH                                       J-3 (Q=SO.sub.2, R.sub.4 =R.sub.5 =CH.sub.3, m=0, R.sub.16 =H)                                           0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =CH.sub.3, m=0, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 = -n-C.sub.4 H.sub.9, m=0, R.sub.16 =H)                                                    0  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      1  O    CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-4 (R.sub.17 =H, m=0, R.sub.16 =H)                                                                      0  O    CH.sub.3                                                                           N                                        J-5 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           N                                        J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         1  O    CH.sub.3                                                                           CH                                       J-6 (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-7 (R.sub.7 =Cl)         0  O    CH.sub.3                                                                           CH                                       J-8 (m=0, R.sub.16 =H)    0  O    CH.sub.3                                                                           CH                                       J-8 (m=0, R.sub.16 =H)    0  O    CH.sub.3                                                                           N                                        J-8 (m=1, R.sub.18 =CH.sub.3, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-9 (R.sub.8 =CH.sub.3)   0  O    CH.sub.3                                                                           CH                                       J-10                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-10                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =Br, R.sub.21 =H)                                                      0  O    CH.sub.3                                                                           CH                                       J-11                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-12                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-13                                                                               (R.sub.19 =CH.sub.3, R.sub.20 =CO.sub.2 CH.sub.3, R.sub.21 =H)                                       0  O    CH.sub.3                                                                           CH                                       J-14                                                                               (R.sub.6 =CO.sub.2 CH.sub.3)                                                                         0  O    CH.sub.3                                                                           CH                                       J-15                                                                               (R.sub.3 =SO.sub.2 CH.sub.3)                                                                         0  O    CH  CH                                       J-16                                                                               (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                               0  O    CH.sub.3                                                                           CH                                       J-16                                                                               (m=0, R.sub.22 =CH.sub.3, R.sub.16 =H)                                                               1  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                            0  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 = H, R.sub.16 =H)                                                           1  O    CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =H, R.sub.16 =H)                                                            0  NCH.sub.3                                                                           CH.sub.3                                                                           CH                                       J-17                                                                               (m=0, R.sub.23 =R.sub.24 =Cl, R.sub.16 =H)                                                           0  O    CH.sub.3                                                                           CH                                       __________________________________________________________________________

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

    ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulations or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See. J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 6 Wettable Powder

    ______________________________________                                         Methyl 2-[[(2-dimethylaminosulfonylphenyl)-                                                              80%                                                  sulfonylamino]carbonyl]-4,6-dimethylpyridin-                                   3-carboxylate                                                                  sodium alkylnaphthalenesulfonate                                                                         2%                                                   sodium ligninsulfonate    2%                                                   synthetic amorphous silica                                                                               3%                                                   kaolinite                 13%                                                  ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 7 Wettable Powder

    ______________________________________                                         N'--[(3-cyano-4,6-dimethylpyridin-2-yl)-                                                                50%                                                   aminocarbonyl]-N,N--dimethyl-1,2-benzene-                                      disulfonamide                                                                  sodium alkylnaphthalenesulfonate                                                                         2%                                                   low viscosity methyl cellulose                                                                           2%                                                   diatomaceous earth       46%                                                   ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 8 Granule

    ______________________________________                                         Wettable Powder of Example 7                                                                           5%                                                     attapulgite granules   95%                                                     (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 9 Extruded Pellet

    ______________________________________                                         Methyl 2-[[N--(2,6-dimethyl-5-nitropyrimidine-                                                            25%                                                 4-yl)aminocarbonyl]aminosulfonyl]benzoate                                      anhydrous sodium sulfate   10%                                                 crude calcium ligninsulfonate                                                                              5%                                                 sodium alkylnaphthalenesulfonate                                                                           1%                                                 calcium/magnesium bentonite                                                                               59%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 10 Oil Suspension

    ______________________________________                                         Methyl 2-[[N--(3-cyano-4,6-dimethylpyridin-2-yl)-                                                          25%                                                aminocarbonyl]aminosulfonyl]benzoate                                           polyoxyethylene sorbitol hexaoleate                                                                         5%                                                highly aliphatic hydrocarbon oil                                                                           70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 11 Wettable Powder

    ______________________________________                                         Methyl 2-[[N--(2,6-dimethyl-5-nitropyrimidine-4-                                                          20%                                                 yl)aminocarbonyl]aminosulfonyl]benzoate                                        sodium alkylnaphthalenesulfonate                                                                          4%                                                  sodium ligninsulfonate     4%                                                  low viscosity methyl cellulose                                                                            3%                                                  attapulgite                69%                                                 ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 12 Low Strength Granule

    ______________________________________                                         Methyl 2-[[N--(3-cyano-4,6-dimethylpyridin-2-yl)-                                                         1%                                                  aminocarbonyl]aminosulfonyl]benzoate                                           N,N--dimethylformamide     9%                                                  attapulgite granules       90%                                                 (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 13 Aqueous Suspension

    ______________________________________                                         N'--[(3-cyano-4,6-dimethylpyridin-2-yl)aminocar-                                                          40%                                                 bonyl]-N,N--dimethyl-1,2-benzenedisulfonamide                                  polyacrylic acid thickener 0.3%                                                dodecylphenol polyethylene glycol ether                                                                   0.5%                                                disodium phosphate         1%                                                  monosodium phosphate       0.5%                                                polyvinyl alcohol          1.0%                                                water                      56.7%                                               ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 14 Solution

    ______________________________________                                         Methyl 2-[[(2-dimethylaminosulfonylphenyl)sulfonyl-                                                          5%                                               amino]carbonylamino]-4,6-dimethylpyridin-3-                                    carboxylate, sodium salt                                                       water                        95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 15 Low Strength Granule

    ______________________________________                                         Methyl 2-[[N--(2,6-dimethyl-5-nitropyrimidine-4-yl)-                                                      0.1%                                                aminocarbonyl]aminosulfonyl]benzoate                                           attapulgite granules      99.9%                                                (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 16 Granule

    ______________________________________                                         N'--[(3-cyano-4,6-dimethylpyridin-2-yl)aminocar-                                                          80%                                                 bonyl]-N,N--dimethyl-1,2-benzenedisulfonamide                                  wetting agent               1%                                                 crude ligninsulfonate salt (containing                                                                    10%                                                 5-20% of the natural sugars)                                                   attapulgite clay            9%                                                 ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 17 High Strength Concentrate

    ______________________________________                                         Methyl 2-[[(2-dimethylaminosulfonylphenyl)sul-                                                             99%                                                fonylamino]carbonylamino]-4,6-dimethylpyridin-                                 3-carboxylate                                                                  silica aerogel             0.5%                                                synthetic amorphous silica 0.5%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 18 Wettable Powder

    ______________________________________                                         Methyl 2-[[(2-dimethylaminosulfonylphenyl)sul-                                                             90%                                                fonylamino]carbonylamino]-4,6-dimethylpyridin-                                 3-carboxylate                                                                  dioctyl sodium sulfosuccinate                                                                             0.1%                                                synthetic fine silica      9.9%                                                ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 19 Wettable Powder

    ______________________________________                                         Methyl 2-[[N--(3-cyano-4,6-dimethylpyridin-2-yl)-                                                         40%                                                 aminocarbonyl]aminosulfonyl]benzoate                                           sodium ligninsulfonate     20%                                                 montmorillonite clay       40%                                                 ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 20 Oil Suspension

    ______________________________________                                         N'--[(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]-                                                      35%                                               N,N--dimethyl-1,2-benzenedisulfonamide                                         blend of polyalcohol carboxylic                                                                              6%                                               esters and oil soluble petroleum                                               sulfonates                                                                     xylene                       59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 21 Dust

    ______________________________________                                         Methyl 2-[[N--(3-cyano-4,6-dimethylpyridin-2-yl)-                                                          10%                                                aminocarbonyl]aminosulfonyl]benzoate                                           attapulgite                 10%                                                Pyrophyllite                80%                                                ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention are active herbicides. They appear to have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. In addition, test results indicate that certain compounds are useful for selective pre- and post-emergence weed control in sugar beets. Alternatively, the subject compounds are useful for plant growth modification.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or herbicides, the species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.06 to 10 kg/ha, the lower rates being suggested for use as selective pre- and post-emergent herbicides in sugar beets, for use in lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types and mefluidide.

The herbicidal and plant growth modifying properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

TEST A

Seeds of crabgrss (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium pensylvanicum), sorghum, corn, soybean, sugar beet, rice, wheat, cotton, and purple nutsedge (Cyperus rotundus) tubers were planted and treated pre-emergence with the test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species, along with cotton and bush bean, were treated with a soil/foliage application. At the time of treatment, the plants ranged in height from 2 to 18 cm. Treated plants and controls were maintained in a greenhouse for sixteen days, after which all species were compared to controls and visually rated for response to treatment. The ratings, summarized in Table A, are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis or necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

The data indicate that at the low rates of application selected for these evaluations, most of the compounds tested are highly active herbicides. Additionally, they often possess plant growth modifying properties, such as causing growth retardation or axillary stimulation.

COMPOUNDS ##STR45##

    TABLE A       Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6      Compound 7 Rate g/ha 50 400 50 400 50 400 50 400 50 400 50 400 2,000 50      400        POST-EMERGENCE Bush bean 1C,1H 4C,8G,6Y 5C,9G,6Y 5C,9G,6Y 5C,9G,6Y      6C,9G,6Y 3C,8G,6Y 4C,9G,6Y 2C,2G,6Y 6C,9G,6Y 6Y 2C,6G,6Y 5S,9D,6Y      5C,9G,6Y 9C Cotton 0 2C,3G 4C,9G 4C,9G 5C,8G 5C,9G 2C,4G 4C,8H 1C 5C,7H      1C,1H 2C,2H 5C,9G 5C,9G 6C,9G Morningglory 2C,3G 3C,5H 4C,8H 5C,9G 4C,9G      5C,9G 3C,7G 4C,8H 3C,5G 4C,7H 1H 2C,5H 10C 4C,7G 4C,9G Cocklebur 0 1C      4C,8H 5C,9G 3C,7G 5C,9G 0 5C,9H 0 2G 2C,8G 2C,8G 4C,9G 5C,9G 10C      Sicklepod 0 2C 2C,3H 5C,9H 4C,7H 4C,9H 1C 3C,5G 0 1C 2C 2C,5G 5C,9G      4C,8G 6C,9G Nutsedge 0 2C,8G 0 2C,7G 2C,9G 3C,9G 2C,5G 3C,8G 7G 9G 0      2C,6G 9G 9C 10C Crabgrass 1C,3G 2C,8G 2C,5H 3C,9H 2C,7H 4C,9G 2G 3C,8H 0      1C,5G 4G 2C,7G 3C,6G 4C,8G 9C Barnyardgrass 2C,6H 4C,9H 5C,9H 9C 5C,9H      9C 2C,7H 5C,9H 0 2C,7H 2C,5H 5C,9H 2C,9H 9C 9C Wild Oats 2C,6G 4C,9H      3C,9G 5C,9G 2C,9H 6C,9G 2C,6G 5C,9G 2C,5G 2C,9G 2G 2C,8G 2C,9G 6C,9G 9C      Wheat 2C,9G 4C,9H 3C,9G 5U,9G 1C,9G 5U,9G 2C,3G 3C,9G 2C,5H 3C,9G 0 4G      2C,9G 9C 9C Corn 3C,9H 5C,9G 2U,9H 10C 5C,9G 5C,9G 3C,8H 5C,9G 3C,7H      3C,9G 2C,8H 2U,9G 9G 9C 10C Soybean 1C,2H 2C,6G 3C,9G,5X 5C,9G 3C,9G,5X      5C,9G 2C,3H 4C,9H 2C,4H 3C,9G 1C,2H 1C,5H 2C,8G 5C,9G 9C Rice 2C,8G      5C,9G 5C,9G 6C,9G 9C 9C 5C,9G 5C,9G 2C,8G 5C,9G 2C,6G 5C,9G 4C,9G 5C,9G      5C,9G Sorghum 5C,9H 5C,9G 5C,9G 9C 4C,9G 9C 2C,8H 2C,9G 3C,5H 5C,9H      2C,5H 3C,9G 9G 9C 10C Sugar beet 0 2C,5H 4C,8G 5C,9G 5C,9G 9C 3C,6H      4C,9G 1C 4C,8G 2C,6H 2C,9G -- 9C 9C PRE-EMERGENCE Morningglory 2C,2H      2C,3H 2C,2H 2C,8G 3C,6H 5C,9G 2C,3H 9C 3C,3H 3C,5H 2G 9G 9G 2C,7G 9C      Cocklebur 0 2C 0 2C,8H 0 4C,7H 2C 3C,3H 0 1H -- -- -- 9C -- Sicklepod 0      0 0 2C,3G 2C 5C,6H 2C,9H 3C 1C 2C 1C 2C,7G 2C,4G 3C,3H 9C Nutsedge 0 0 0      0 2G 2C,7G 0 2C,5G 0 0 10E 10E 10E 1C,9G 10E Crabgrass 0 0 0 2C 0 2C,4G      2G 3C,6G 0 1C 0 0 3C,8G 1C 5G Barnyardgrass 0 0 0 2C,6G 2C 3C,8H 1C      3C,3H 0 1C 0 2C,4H 3C,9H 2C,7H 5C,9H Wild Oats 2G 5G 4G 3C,7G 4C,8G      4C,9H 2C,9H 5C,9G 1C,2G 3C,7G 0 2C,8G 3C,7G 2C,9H 3C,9H Wheat 2G 8G 4G      3C,8H 2C,9H 4C,9G 2C,9H 4C,9G 1C,2G 2C,9H 3G 2C,9G 2C,9H 2C,9G 3C,9H      Corn 0 2C,6H 3C,8G 5C,9H 3C,9H 4C,9H 5C,9H 5C,9G 2C,5G 5C,9H 2C,4G 2C,9G      9G 5C,9G 10H Soybean 0 1C 1C 3C,5H 3C,5H 4C,6H 2C 4C,8H 2C,3G 3C,4H 0 1H      3C,5H 8H 9H Rice 0 2C,4G 3C,6H 10E 3C,7H 10E 2C,7H 5C,9H 2C 2C,4G 0 9H      10E 10E 10E Sorghum 3C,6G 5C,9G 5C,9H 10H 7C,9H 7C,9H 5C,9H 5C,9H 2C,6G      5C,9H 2C 2C,9G 2C,9H 7C,9H 6C,9H Sugar beet 0 0 2C,5H 3C,8G 2C,2H 5C,9G      2C,2H 3C,8H 0 0 0 0 -- 4C,9G 5C,9G Cotton -- -- -- -- -- -- -- -- -- --      -- -- -- -- --        Cmpd. 8 Cmpd. 9  Cmpd. 10 Cmpd. 11 Cmpd. 12 Compound 13 Cmpd. 14 Cmpd.      15 Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd. 22 Rate      g/ha 50 50 50 50 50 50 400 50 50 50 50 50 50 50 400 400        POST-EMERGENCE Bush bean 4C,8G,6Y 2C 1C 1C,1H 1C 3C,6G,6Y 5C,9G,6Y 0      2C,3H,6Y 1C -- -- -- -- 2C 4C,9G,6Y Cotton 4C,8H 2C,2H 1C 4C,5H 2C 4C,6H      5C,8H 0 2C,5G 1C,4G 2C,8G 6C,9G 2C,5G 3C,8G 2C 3C,6H Morningglory 4C,9G      3C,6G 2C 2C,5G 2C 2C,4G 4C,8H 0 2C,6H 1C 2C 4C,8H 2C,3H 4C,8H 2C,5G      3C,8G Cocklebur 9C 2C 0 4C,9G 2C 3C,9G 5C,9G 0 2C 1C,5H 3C,9H 10C 4C,9G      4C,8H 5C,9G 9C Sicklepod 3C,5G 2C 0 3C,5G 1C 2C,4H 4C,8G 0 0 0 2C 10C      2C,2H 4C,5G 3G 3C,5G Nutsedge 3C,6G 2G 0 5C,9G 0 2C,9G 4C,9G 0 0 0 8G 9C      5G 3G 3G 2C,7G Crabgrass 3C,9G 2C,5G 0 6H 0 2C 3C,7G 0 0 0 2G 8G 4G 5G 0      2C,7G Barnyardgrass 5C,9G 2C,8H 2C,3H 5C,9H 0 3C,8H 5C,9H 0 0 0 1H 9H 5H      2C,5H 2H 3C,8H Wild Oats 4C,9G 2C 0 2C,5G 0 1C 2C,8G 0 0 0 0 2C,9G 3G      3C,9G 0 3C,9H Wheat 2C,9G 2C,8G 0 1C,2G 0 1C,2G 1C,7G 0 0 0 0 3C,9G 6G      3C,9G 0 2C,9G Corn 9C 2C,9G 1C 2C,9G 2C,6H 1C,9G 5U,9G 0 0 0 1C,3G 3U,9G      2C,8H 2C,7H 2G 3C,9G Soybean 5C,9G 2C,8G 1C 2C,9G 1C 2C,8H 4C,9G 0 0      1C,7G,7X 5C,9G 5C,9G 3C,9G 4C,9G 1C 3C,8H Rice 5C,9G 2C,8G 0 5C,9G 1C,8G      2C,9G 9C 0 0 2H 9G 4C,9G 9G 5C,9G 6G 5C,9G Sorghum 9C 2C,9G 2C,8H 3C,9H      0 3C,7H 2C,9G 0 0 1C,3H 2G 9G 3C,8H 4C,9G 1B 3C,9G Sugar beet 3C,5H 2C      2C 5C,9G 2C,5H 4C,9G 9C 2C,2H 3C,6G 1C,2H 3C,8G 5C,9G 2C,2G 3C,8H 4B      3C,8H PRE-EMERGENCE Morningglory 9G 0 0 8G 3C 2C,4G 2C,9G 0 1C,5H 1H 2G      7H 9G 2C,8H 3C,9G 5C,9G Cocklebur 8H -- 0 2C,8H 0 2C 2C,9H 0 2H 0 3G 8H      2C,5G -- 9H 9H Sicklepod 0 0 0 2H 1C 0 2C,9G 0 2H 0 4G 9G 2C 2C 8G 9G      Nutsedge 0 0 0 9G 0 5G 10E 0 0 0 10E 10E 0 2C 2C,8G 4G Crabgrass 0 0 0      1C 0 1C 2C,4G 0 2G 0 2G 5G 2G 2G 0 2G Barnyardgrass 4H 0 0 2C,3H 0 1C      2C,8H 0 5G 1C 1H 2C,8G 1H 2C,2H 1C 2C,9H Wild Oats 1C 0 0 2C,7G 0 4G      2C,8G 0 0 0 0 2C,8G 2G 2C,5G 0 3C,9G Wheat 2C,8H 0 0 2C,8G 0 5G 2C,8G 0      0 0 0 2C,8H 2G 7G 0 9H Corn 2C,8H 5G 0 2C,9G 2C,5G 2C,9H 2C,9H 1H 0 0 2G      2C,9H 3C,6G 2C,8G 6G 2C,9H Soybean 1C 1C 1C 3C,5H 1C 2C,5G 2C,7H 0 0 0      2H 2C,2H 0 2H 1C 3C,7H Rice 2C,8G 0 0 10E 2C 2C,7G 2C,8G 0 3G 1C 6G 10E      9H 9H 3C,8H 10E Sorghum 2C,9H 3G 5G 3C,8H 0 2C,5G 2C,7G 2G 2G 1H 3G      3C,9H 2C,7G 3C,9G 0 5C,9H Sugar beet 8G 1C 1C 6C,9G 0 4C,9G 5C,9G 0 0 5G      4G 3C,8G 1C 2C 9G 9G Cotton -- -- -- -- -- -- -- -- -- -- 3G 2C,8G 0 2G      -- --        Cmpd. 23 Cmpd. 24 Compound 25 Compound 26 Compound 27 Compound 28      Compound 29 Compound 30 Cmpd. 31 Cmpd. 32 Cmpd. 33 Cmpd. 34 Cmpd. 35      Rate g/ha 400 400 400 50 400 50 400 50 400 50 400 50 400 50 50 50 50 50      50        POST-EMERGENCE Bush bean 1C,3H,6Y 2C,7G,6Y                 Cotton      3C,5G 2C,5H 2C,4G 0 2C,4G 0 3C,9H 2C,5H 3C,6H 2G 5C,9G 2C,9H 5C,9G 2C,9H      7G,2C 9C 5C,9G 2G 3C,8H Morningglory 4C,9G 3C,8H 1C,1H 0 1C,1H 0 5C,9G      1C,2G 3C,6G 3G 5C,9G 3C,8H 5C,9G 3C,6G 1C 2C,4G 1C,2H 2G 2G Cocklebur 8H      4C,9G 3C,4G 0 3C,9H 0 5C,9G 3C,9H 4C,9H 3C,7G 10C 3C,9G 9C 4C,9G 2C,8H      4C,9G 3C,9H 2C,8H 3C,8H Sicklepod 1C,2H 3C,5G 3C,5G 0 3C 0 4C,5G 2C      3C,3G 3C,5G 6C,9G 4C,7G 5C,9G 4C,8H 2C 5C,9G 3C,8H 0 0 Nutsedge 3G 4G 0      0 0 0 3G 0 0 0 9G 2C,6G 5G 2G 3C,9G 2C,9G 2C,8G 0 5G Crabgrass 2C,9G      3C,8G 0 0 0 0 4G 0 0 0 4C,9G 3G 7G 3G 0 0 3G 0 1C Barnyardgrass 2C,5H      3C,9H 0 0 0 0 3C,7H 2H 0 0 9C 5C,8H 3C,8H 4H 0 2G 2C,4H 2C,7H 2C,5H Wild      Oats 2C,9H 2C,4G 0 0 0 0 3C,9G 3G 0 0 3C,8G 3G 3C,7G 0 0 2C,9H 0 2C,5G 0      Wheat 2C,9G 4G 0 0 0 0 8G 2G 0 0 5G 0 5G 6G 0 9C 7G 2C,5G 0 Corn 2C,8H      2C,8H 2G 0 0 0 1H 0 0 0 3C,9G 2C,8H 3C,7H 2C,4H 0 5C,9G 3C,8H 3C,9H      2C,8H Soybean 1C,5H 3C,8G,5X 2C,2H 0 3C,3H 0 5C,9G 2C,2H 3C,3G 0 5C,9G      3C,9G 5C,9G 3C,9G,7X 1H 4C,9G 3C,8H 1C 1C,1H Rice 5C,9G 4C,9G 2G 0 1C 0      4C,9G 2C,5G 0 0 6C,9G 6C,9G 5C,9H 2C,9G 6G 5C,9G 9G 9G 2C,8G Sorghum      2C,9G 9G 1C 0 0 0 3C,7H 2H 3C,4G 0 6C,9G 3C,9G 3C,9H 3C,7H 0 2C,9H 3C,9H      2C,9G 2C,8H Sugar beet 3G 4C,8H 2C,6H 0 3C,7G 0 4C,8G 3C,6H 3C,6G 3C,6H      9C 5C,9G 5C,9G 3C,8H 9C 9C 2C,3G 3C,6G 3C,6G PRE-EMERGENCE Morningglory      2C,6H 3C,9G 1C 0 1C,1H 0 2C,2H 0 3C,5H 0 9G 3C,7H 8G 2C,6G 2H 0 2G 0 0      Cocklebur 6H 9H 0 0 2C,2H 0 2C,3H 1H 4C,7G 0 9H 9H 9H 3C,7H 2H 2C,7H      2C,5H 0 0 Sicklepod 2C,4G 7G 0 -- 0 0 2C,5H 0 2C,5G 0 3C,8G 4C,5G 3C,7G      2C,5G 2G 2C 0 0 0 Nutsedge 0 5G 0 0 0 0 0 0 0 0 2C,5G 0 0 0 5C,9G 10E      2C,5G 0 0 Crabgrass 2C,5G 1C 0 0 0 0 0 0 0 0 2C 1C 0 0 2C 0 2G 0 0      Barnyardgrass 5H 2C,8H 2G 0 2H 0 1H 0 0 0 3C,9H 2C,3H 3C,6G 0 1C 1C 2C 0      0 Wild Oats 2C,9G 2C,7G 0 0 0 0 0 0 0 0 3C,8G 1C 3C,6G 1C 0 2C,8G 2C 0 0      Wheat 9H 8G 0 0 0 0 0 0 2G 0 2C,7G 1C 6G 0 0 2C,8G 4G 0 0 Corn 2C,9G      2C,9H 2G 0 0 0 5G 2C,3G 2C,5G 0 10H 3C,9H 3C,8G 2C,6G 5G 2C,9H 3C,8H 3G      2G Soybean 1C,1H 2C,3H 0 0 -- 0 2C 0 2C 0 8H 2C,5H 3C,6H 2C,4G 0 2C -- 0      0 Rice 10E 10E 0 0 0 0 2C 0 2C 0 10E 3C,5G 4C,7G 2C,5G 0 3C,8H 3C,5G 0 0      Sorghum 3C,9H 5C,9G 2G 0 3G 0 2C,3G 5G 2C,4G 0 5C,9H 2C,9G 3C,9H 3C,7G 0      2C,9G 3C,6G 2G 0 Sugar beet 8G 5C,9G 5H 0 0 0 3C,7G 2C,7H 2C,6H 0 5C,9G      3C,8G 5C,9G 2C,8G 5C,9G 5C,9G 8G 7H 7H Cotton -- -- 0 0 0 0 2C,7G 0 2G 0      9G 3C,7G 8G 2C,6G 6G 8G 5G 1C 0         Cmpd. 36 Cmpd. 37 Cmpd. 38 Cmpd. 39 Cmpd. 40 Cmpd. 41 Cmpd. 42 Rate      g/ha 50 50 50 50 50 50 50        POST-EMERGENCE Bush bean         Cotton 2C,8G 2C,9G 2G 6G 3G 2G 2G      Morningglory 2C,3G 1C 2G 3G 1C,3G 3C,6H 2C,5G Cocklebur 3C,9G 9C 1C      2C,8G 3C,8G 2C,6H 3C,8G Sicklepod 2C 3C,7G 0 3G 0 3G 3C,5G Nutsedge      3C,8G 3C,7G 0 0 0 0 3G Crabgrass 4G 6G 0 0 0 0 2G Barnyardgrass 3C,9H 9C      6H 0 0 5H 3C,6H Wild Oats 2C,8G 9C 0 0 0 0 2C,5G Wheat 1C,7G 6C,9G 0 0 0      2G 2C,8G Corn 1C,9G 3C,9G 1H 0 0 2C,7H 2C,6H Soybean 2C,9G 5C,9G 3H      1C,2G 3H 2C,2H 2C,2H Rice 5C,9G 5C,9G 4G 6G 6G 2C,8G 2C,5G Sorghum 3C,9H      5C,9G 2C,6G 3C,8H 2C,8H 2H 1C Sugar beet 2C,4G 5C,8G 1H 2C,5G 1C,3H      2C,6H 2C,7G PRE-EMERGENCE Morningglory 2G 3C,6G 0 2C,3H 0 7H 0 Cocklebur      8H 9H 2H 9H 9H 2G 0 Sicklepod 2G 5G 1C 1C 0 0 0 Nutsedge 3G 2G 0 0 0 0 0      Crabgrass 0 0 0 0 0 0 0 Barnyardgrass 4H 5G 0 0 0 2H 0 Wild Oats 2G      3C,9G 0 0 0 0 0 Wheat 0 2C,5G 0 0 0 0 0 Corn 2C,5G 2C,9H 0 2C,7G 0 2G 0      Soybean 2C,2H 1C,1H 1H 0 1C 1H 0 Rice 3C,8H 5C,9H 0 0 0 5G 0 Sorghum      3C,6G 5C,9H 0 0 2C 0 0 Sugar beet 7G 9H 0 6G 2H 0 0 Cotton 5G 9G 2G 3G      2G 0 0

The following test was performed to better define the pre-emergence activity of the claimed compounds.

TEST B

Two plastic bulb pans were filled with fertilized and limed Woodstown sandy loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. Results for several of the more active compounds are presented in Table B. Almost all of the compounds tested showed pre-emergence activity on a number of species at rates as low as 31 g/ha; some were active at even lower rates. At higher rates, e.g. 125 g/ha, most compounds exhibited broad spectrum pre-emergence activity.

                  TABLE B                                                          ______________________________________                                         PRE-EMERGENCE ON                                                               WOODSTOWN SANDY LOAM                                                                    Compound 7                                                                              Compound 8 Compound 22                                       Rate g/ha  8      62      31   250   31    125                                 ______________________________________                                         Crabgrass  0      0       0    7G    0     3G                                  Barnyardgrass                                                                             0      7G      0    5G    0     3G                                  Sorghum    6G     9G      8G   9G    9G    10C                                 Wild Oats  0      2G      0    0     0     3G                                  Johnsongrass                                                                              5G     9G      4G   8G    4G    5G                                  Dallisgrass                                                                               0      4G      0    5G    0     7G                                  Giant foxtail                                                                             0      0       0    7G    3G    8G                                  Ky. bluegrass                                                                             0      5G      2G   9G    6G    10C                                 Cheatgrass 0      9G      0    7G    7G    10C                                 Sugar beets                                                                               5G     9G      5G   7G    6G    8G                                  Corn       7G     8G      3G   7G    3G    9G                                  Mustard    9G     9G      8G   9G    8G    9G                                  Cocklebur  0      8G      --   8G    7G    7G                                  Nutsedge   0      9G      0    6G    2G    4G                                  Cotton     3G     3G      3G   5G    2G    8G                                  Morningglory                                                                              0      2G      0    0     2G    2G                                  Sicklepod  0      3G      2G   3G    0     2G                                  Teaweed    3G     6G      0    0     0     0                                   Velvetleaf 0      2G      0    2G    2G    4G                                  Jimsonweed 2G     4G      0    0     2G    7G                                  Soybean    0      7G,7H   0    2G    0     3G                                  Rice       6G     10C     5G   10C   10C   10C                                 Wheat      0      6G      0    8G    0     2G                                  ______________________________________                                    

The following test was performed to better define the post-emergence activity of the claimed compounds.

TEST C

The test chemicals, dissolved in a non-phytotoxic solvent, were applied in an overall spray to the foliage and surrounding soil of selected plant species. One day after treatment, plants were observed for rapid burn injury. Approximately fourteen days after treatment, all species were visually compared to untreated controls and rated for response to treatment. The rating system was as described previously for Test A. The data are presented in Table C.

All plant species were seeded in Woodstown sandy loam soil and grown in a greenhouse. The following species were grown in soil contained in plastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa, corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), morningglory (Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthium pensylvanicum), crabgrass (Digitaria sp.), nutsedge (Cyperus rotundus), barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii) and wild oats (Avena fatua). The following species were grown in soil in a paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, and mustard. All plants were sprayed approximately 14 days after planting. Additional plant species are sometimes added to this standard test in order to evaluate unusual selectivity.

Results for two of the most active compounds tested in this screen are presented in Table C. Many of the other compounds also showed post-emergence activity at rates as low as 4 or 16 g/ha.

                  TABLE C                                                          ______________________________________                                         Over-the-Top Soil/Foliage Treatment                                                   Compound 7    Compound 8                                                Rate g/ha                                                                               4       16      61    4     16    61                                  ______________________________________                                         Soybeans 10C     10C     10C   8G,9C 10C   10C                                 Velvetleaf                                                                              7G,7C   9C      10C   6G    9G,7C 10C                                 Sesbania 7G      9G      9G    8G    9G    9G                                  Sicklepod                                                                               7G      9G      9G    4G    8G    9G                                  Cotton   9G      10C     10C   9G    9G    10C                                 Morning- 7G,5C   8G      8G    7G    7G,6C 8G,7C                               glory                                                                          Alfalfa  7G,6C   7C,8G   8C,9G 2G,1C 7G,6C 10C                                 Jimsonweed                                                                              4G      6G      9G    0     4G    6G                                  Cocklebur                                                                               8G      9G      9G    8G    9G    10C                                 Sunflower                                                                               8C,7G   10C     10C   8G    10C   10C                                 Mustard  6G      8G      10C   7G    8G    9G                                  Sugar    8G      10C     10C   7G    8G    10C                                 beets                                                                          Corn     10C     10C     10C   6G    7G    7G                                  Crabgrass                                                                               6G      3G      6G    4G    7G    9G                                  Rice     9C      8C,8G   9C    6G    9C    10C                                 Nutsedge 7G      7G      7G    0     2G    4G                                  Barnyard-                                                                               10C     10C     10C   7G    9C,7G 10C                                 grass                                                                          Wheat    6C,7G   6G      6C,7G 6G    7G    8G                                  Giant    9G      6G      9G    3G    6G    8G                                  foxtail                                                                        Wild Oats                                                                               8G      8G      8G    5G    7G    8G                                  Sorghum  9G      9G      9G    8G    9G    9G                                  Johnson- 9G      9G,9C   9G    8G    9C    9C                                  grass                                                                          Field    7G      5G      7G    0     2G    4G                                  Bindweed                                                                       ______________________________________                                    

TEST D

Two 25-cm in diameter plastic pans lined with polyethylene liners were filled with prepared Sassafras loamy sand soil. One pan was planted with seeds of wheat (Tritricum aestivum), barley (Hordeum vulgare), wild oats (Avena fatua), blackgrass (Alopecurus myosuroides), annual bluegrass (Poa annua), green foxtail (Setaria viridis) and Italian ryegrass (Lolium multiflorum). The other pan was planted with seeds of wild radish (Raphanus naphanistrum), kochia (Kochia scoparia), Matricaria inodora, black nightshade (Solanum nigrum), wild mustard (Brassica kaber), wild buckwheat (Polygonum convolvulus), Galium aparine, Veronica persica and sugar beets (Beta vulgaris). The above two pans were treated pre-emergence. At the same time two pans in which the above plant species were growing were treated post-emergence. Plant height at the time of treatment ranged from 1-15 cm depending on plant species.

The test compound was diluted with a non-phytotoxic solvent and sprayed over-the-top of the pans. An untreated control and a solvent-alone control were included for comparison. All treatments were maintained in the greenhouse for 21 days at which time the treatments were compared to the controls and the effects visually rated utilizing the rating system as described in Test A. The recorded data are presented in Table D. The data indicate that the compound tested has utility for selective weed control in sugar beets.

                  TABLE D                                                          ______________________________________                                                   Compound 19                                                          Rate g/ha   4       16      64    125   250                                    ______________________________________                                         Pre-Emergence                                                                  wheat       0       0       0     --    --                                     barley      0       0       0     --    --                                     wild oats   0       0       0     --    --                                     ryegrass    0       0       4G    --    --                                     annual bluegrass                                                                           0       1G      4G    --    --                                     blackgrass  0       3G      2G    --    --                                     green foxtail                                                                              0       0       0     --    --                                     Matricaria inodora                                                                         1G      5G      6G    --    --                                     Galium aparine                                                                             4G,3C   4G,3C   7G    --    --                                     kochia      0       0       0     0     0                                      black nightshade                                                                           5G,4C   4G,7C   8G,9C 8G,7C 9G                                     speedwell   3G      10C     10C   --    --                                     wild buckwheat                                                                             0       5G,3C   7G    8G,8C 10C                                    wild mustard                                                                               0       5G,4C   9G,9C 9G    10C                                    wild radish 3G      9G      9G    --    --                                     sugar beets 0       0       0     1G    1G                                     Post-Emergence                                                                 wheat       0       0       3G    --    --                                     barley      0       0       3G    --    --                                     wild oats   0       0       2G    --    --                                     ryegrass    0       0       1G    --    --                                     annual bluegrass                                                                           0       0       0     --    --                                     blackgrass  0       0       0     --    --                                     green foxtail                                                                              0       0       0     --    --                                     Matricaria inodora                                                                         1C      1G,3C   4G,3C --    --                                     Galium aparine                                                                             2G      9G      --    --    --                                     kochia      --      0       3G    0     0                                      black nightshade                                                                           1G,1C   3C      3C    5G,3C 9G,8C                                  speedwell   7G,5C   7G,4C   8G    --    --                                     wild buckwheat                                                                             9G,7C   9G,8C   9G    4G    10C                                    wild mustard                                                                               9G,8C   9G,7C   10C   3G    10C                                    wild radish 10C     10C     10C   --    --                                     sugar beets 0       0       3G    4G,3C 8G,8C                                  ______________________________________                                     

What is claimed is:
 1. A compound of the formula: ##STR46## wherein J is ##STR47## W₁ is O or S; R is H or CH₃ ;R₁ is CO₂ R₉ R₂ is H, C₁ -C₂ alkyl, C₁ -C₂ alkoxy, C₁ -C₂ alkylthio, C₁ -C₂ alkylsulfinyl, C₁ -C₂ alkylsulfonyl, C₁ -C₂ monohaloalkyl, CF₃ or halogen; R₉ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ; A is ##STR48## W is CN; X is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, Cl, CH₂ OH, NHCH₃ or N(CH₃)₂ ; Y is CH₃, OCH₃, OC₂ H₅ or Cl; Z is CH;and their agriculturally suitable salts; provided that (1) X and Y cannot simultaneously be Cl.
 2. A compound of the formula ##STR49## wherein J is ##STR50## R₁ is CO₂ R₉ R₂ is H, F, Cl, Br, CH₃, OCH₃ or CF₃ ;R₉ is C₁ -C₃ alkyl, CH₂ CH═CH₂, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ; R is H or CH₃ ; A is ##STR51## W is CN; X is CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃ or Cl; Y is CH₃, OCH₃, OC₂ H₅ or Cl; and Z is CH;provided that (a) X and Y cannot simultaneously be Cl; and their agriculturally suitable salts.
 3. A compound of claim 1 where R is H and W₁ is oxygen.
 4. A compound of claim 3 where R₁ is CO₂ CH₃ or CO₂ C₂ H₅ ; and R₂ is H, F, Cl, CH₃, OCH₃ or SCH₃.
 5. A compound of claim 4 where X and Y are independently CH₃ or OCH₃.
 6. The compound of claim 1 which is methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 7. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 8. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 2 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 9. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 3 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 10. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 4 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 11. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 5 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 12. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 6 in combination with (a) a surfactant and (b) a solid or liquid diluent.
 13. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 1. 14. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 2. 15. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 3. 16. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 4. 17. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 5. 18. A method of controlling the growth of undesired vegetation comprising applying to the locus of such vegetation an herbicidally effective amount of a compound of claim
 6. 19. A herbicidal comprising an herbicidally effective amount of a compound of claim 1 in combination with a surfactant.
 20. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 1 in combination with a solid or liquid diluent.
 21. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 2 in combination with a surfactant.
 22. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 2 in combination with a solid or liquid diluent.
 23. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 3 in combination with a surfactant.
 24. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 3 in combination with a solid or liquid diluent.
 25. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 4 in combination with a surfactant.
 26. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 4 in combination with a solid or liquid diluent.
 27. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 5 in combination with a surfactant.
 28. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 5 in combination with a solid or liquid diluent.
 29. A herbicidal composition comprising an herbicidally effective amount of a compound of claim 6 in combination with a surfactant.
 30. A herbicidal composition comprising a herbicidally effective amount of a compound of claim 6 in combination with a solid or liquid diluent. 